Red
by griffin blackwood
Summary: K was just another teen before he got the letter which changed his life forever. Soon he found himself dropped head first into the shark infested waters of the Upper East Side, only to learn that his past is not as dead as it should be. He never planned on making friends, let alone falling in love. Why is Chuck protecting him? Starts before the pilot and based on the show. SLASH
1. Everything Has Changed

Disclaimer: I don't own Gossip Girl or any of the associated characters or locations. This is a work of fiction. I don't profit from this in any form. This is my first attempt at a Gossip Girl fic so please bear with me. This will be a slash fic that was inspired by several of my other favorite shows, including Revenge. If you don't like slash you have been warned.

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Our story begins when things changed all one summer day... it started out like any of the others. As a creature of habit he had gone through his daily routine before being presented with the mail. That was when everything became more complicated. The proverbial can of worms had now been opened and he had a difficult decision before him. In the end he took the first of many big risks to come and had been temporarily been rewarded with a bright future, but the good times would not last as there is no such thing as a free lunch, or in this case: a free ticket to living with the elite on the Upper East Side.

He would never be the same, though its difficult to say whether he held all the strings or if he allowed himself to be changed for what one could argue was for the better or for worse. Where there once was a silly boy that dreamed of being a hero, now stood a reluctant teen who had been burned a few times too many. At one time, before bed each night, he would listen to tales of brave cowboys and noble knights. Lately he just prayed for it all to end between pages of his required reading…

On the outside he was picture perfect, but there was so much more that lurked beneath the surface of his handsome physique. The grass is not always greener on the other side after all. Like many of his soon to be peers, he held two distinct personas. And unfortunately for our hero, Gossip Girl was just one of the many individuals gunning for him.

He was about to do what was expected of him, not that really meant much, until he got a text… a text that changed his life forever. And with it, he went from a nobody with no past, to a friend, a target, a lover. He broke hearts and had his heart broken. Said teen was headed to the city that never sleeps to learn of what had happened. He had yet to learn of what happened THAT day and it still haunted him to the core. No matter what people say, there is always someone in your life. Someone who has brought you into the world whether they wanted to or not.

Unfortunately he never got that chance. There are things I am sure you would love to learn about him. But now is not time for dramatics. He may have done a lot of things that he would later regret, but every action has a price. Knowledge is power and no piece of information comes free.

Revenge? No that would be too easy and horribly cliché.

No instead he just wanted to find his place in the world… THEIR world...

…And maybe he really wanted to have some fun shaking up THEIR's while finding his answers…

Watch out ladies and gents, K's going to make his mark and it's not going to be pretty.

The Upper East Side won't know what hit them when Hurricane K takes aim at the city that never sleeps. Any one want to take bets on who will be the first casualty?

My bet's on Lonely Boy...


	2. Speak Now

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show

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Spotted… Arriving at JFK, a male in non-nondescript clothing with what appears to be a Red Sox hat, ruining any attempt at maintaining a fashionable appearance. What is he trying to hide behind those sunglasses? Don't worry I'll get to the bottom of it. You think S's departure from the city was big? Something tells me that this new arrival will be making even bigger waves. Now which of our favorite Upper East Siders is going to be his first victim? I have my eyes and ears on you Mystery Boy. You must be something big to have received the attention of so many of my followers.

XOXO, Gossip Girl

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Sixteen-year-old Kennedy Blake didn't even know what he was doing here. After all, he had just left everything behind in the city of Boston on the off chance he would finally get his hands on the truth of what happened... His memory was a bit hazy of the events that had transpired, but something was not right. Against better judgment, he packed up his few material possessions and took the offered flight to New York to begin a new chapter in his life.

For once in his life, everything was neatly laid out and planned accordingly for him ahead of time. Every detail from his housing to education was planned to the most minute detail. He was sure that he was going to stick out like a sore thumb, but there were worst things that could happen. Its not like he had gone gallivanting around the world drinking and doing drugs like a certain heiress we all know.

No instead he was more afraid of his past coming… He had skeletons in his closet, some that he knew of and other that were buried away by someone else.

Compared to his last few years, this was a dream come true. If you had asked him a year ago if he thought this possible, he would have said no. But then again this is the present and not a year ago.

Apparently a certain prestigious school in New York had sent out an acceptance letter after they learned that he was alive. Said letter informed him of the fact that there was a spot saved there for him by his parents… since birth? He thought it odd quite frankly as he had spent his entire life several hours away in Massachusetts, and so had his parents to the best of his knowledge. He didn't know much about his extended family but it looked like all of them were living in the Bay State… Or at least that's what he recalled off the top of his head.

Of course this may have been a bigger part of someone's master plan but what did he honestly have to lose? It's not like he was a pawn in someone's game after all. That would be too ridiculous! After all that sounded a lot more like a teen drama than his life.

Things began to make a turn one fateful day…

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Kennedy had a few days to go until school began, but he wanted to become a little more familiar with his surroundings. The administration had been surprisingly warm and helpful. They reassured him that his parents had set aside funds for his education years ago and they just happened to learn of his existence by chance a few weeks prior after an audit. They knew between his academics and skills in soccer that he would fit in quickly and soon be off to a great university… now if only things were that easy.

He had already been in the city for a few weeks. It was hard to believe that he had already entered the new chapter of his life over a month ago. It seemed like just yesterday that everything changed. It all started with a letter and a phone call.

In fact it was still saved on his phone. Kennedy kept it to make sure that this wasn't a dream. It was too good to be true, but at the same time he jumped at the chance to break free immediately. It's not like he had much of a decision anyway.

He didn't like the fact that he would be entering his junior year in a brand new city and a new school without a single person to rely on... well that was a bit of a lie. So far he had the mysterious benefactor that had agreed to help with his expenses. Kennedy knew that he would meet them eventually, praying that there were no strings attached to this generosity. It could be a benevolent alumnus donating to need based students or it could be an alumnus or outside party doing so to keep a closer eye on him for the time being. The teen was leaning more toward to philanthropy than malicious planning.

While no teen heartthrob, Kennedy was far from ugly. In fact he was quite handsome. Between his ebony hair to his tanned skin, he was quite attractive. His time spent doing odd jobs, and playing several sport—mainly soccer and lacrosse, had definitely help tone his body. Despite all of this he was quite self-conscious about himself in general physically, mentally, and spiritually. Each and every day could be his last so he tried to live life to the fullest, but that wasn't easy when you have to support yourself.

Kennedy was provided with a small apartment near the campus of Columbia University. Several young alumni lived in the area and checked in on him from time to time. While much of it was forced pleasantries, Kennedy genuinely enjoyed their company. It felt odd to have people keeping an eye on him as he had lived on his own for so long, but it was a small price to pay. One alumnus, a mellow blonde, in particular told the Boston native to watch himself. Kennedy didn't take the Upper East Sider seriously until his acquaintance whipped out his smartphone and logged onto a certain website.

And then it all came crashing down… Two words would forever change his life… Gossip Girl. Who knew a gossip site about "normal" people could be even more entertaining than the celebrity tabloids. He was never one to pay much attention to following the lives of the rich famous. It was difficult enough to take care of himself, he had to devote every moment to supporting himself. The stipend he received didn't cover much, but it was enough that he could choose to not get a part time job if he was frugal.

Kennedy found himself the subject of one of Gossip Girl's blasts much to his ire and confusion. He was Mystery Boy. The nickname could have been much worse, but he was wondering how they found him in the first place. For someone who initially had no connection to the Upper East Side, it was interesting that someone who send a blast about him as soon as he arrived in the city. He had yet to figure out why anyone would have felt that he was of any interest, let alone worthy of a tip to the infamous blogger's site.

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"So what exactly are you saying?" Kennedy asked his companion in an irritated tone. He was never one for smoke and mirrors. He was blunt and to the point most of the time, but did bite his tongue once in a while.

"You just need to be careful Kennedy." The teen in question gave the blonde male with him a knowing look. "The walls have eyes."

Our black haired friend sighed. "Just spit it out Connor, you have class in thirty."

The blonde male smiled at Kennedy's concern. While he wasn't the brightest bulb, Connor

Windsor was the most sociable of Kennedy's minders or "manny's" as the teen preferred to label them… In truth, sometimes the roles were reversed between these two. The teen was often mothering the other male who was only a few years older than himself, but you would never guess it with the way the pair acted around each other.

"Do you remember me telling you about how news travels fast on campus?" Connor asked as he finished his coffee. The mug was quietly brought down onto the table.

"Yeah," Kennedy said getting up and placing their mugs in the sink.

"Well, gossip has reached a whole other level than you're used to here. Mixing together jealousy and texting essentially gives you Gossip Girl."

"You have to be kidding me Connor." Kennedy had been dreading something like this happening, but he had no clue Connor was going on now. Things were just always more complicated in New York. It was a fact of life that many accept. But even this was pushing it for him. The teen was used to gossip mills, but making everything anonymous online just sounded like a recipe of disaster.

"I wish I was dude, but I'll have to make this quick. Just read it," the blonde said after pulling up a page on his Blackberry as Kennedy sat back down was a look of disbelief. Connor ran a hand through his blonde locks as he extended his other arm toward the teen, phone in hand. "I'm serious."

"What is this?" Kennedy replied as he took the offered phone.

"Just read."

"Fine." The teen took the item in the outstretched hand and began to focus his brown eyes on the device before him. Kennedy looked at the screen only to be met with an image of his arrival to the big apple. He was far from being egotistical, but he had to admit that the poster got his good side.

"What do you think?" Connor asked with a blank stare.

"Is this some sort of sick joke?" Kennedy was clearly irritated, though he hid his embarrassment over the whole ordeal well.

"You know I'm not one to joke," Connor said as he took his phone back. "Things are completely different from what you're used to. If you don't believe me, look at some of the other things that have been put up there."

"Fine," Kennedy said resigned. "But you better get going, you're going to be late if you don't hurry up."

The duo got up and walked to the door.

"Of course MOM," Connor said with a smile as he ruffled Kennedy's ebony locks. "Mommy always knows best."

"Seriously?" Kennedy replied in a bored tone. "You're so lame. I don't even know why I put up with you."

"You know you love me Kenny!" Connor said in a chipper tone as he took one last look at the clock.

"Keep dreaming Windsor."

"Are you sure you don't want to come to my parents' for dinner tomorrow night? My dad's an excellent cook if I do say so myself. It's going to definitely beat whatever one of the guy's brings you tomorrow night."

"Yeah, I'm sure. I wouldn't want to intrude dude. Maybe next time?" Kennedy tried to come off as polite, but he didn't really feel comfortable with this subject. He knew that he would be meeting the Windsor's at some point, but wasn't ready to do so despite spending so much time with their son already.

An awkward silence quickly sped things up. The teen didn't want to really talk about this subject any further. The twenty-something knew that he had to get going soon if he had any hopes of getting a decent seat, let alone be on time.

"Well I'm off dude. One of the others will be checking in on you this weekend. Text me if you need anything and I mean ANYTHING."

"I'll be fine Connor. I'll see you on Monday. Now get going or you'll be late."

"See you then bro!" Connor said as he departed.

Kennedy looked at the retreating figure for a few moments before closing his door behind him.

While he was not used to let people in close, Connor had quickly wormed his way in, but in a good way. The blonde was an alumnus of St. Jude's School for Boys, the very same elite college preparatory school that Kennedy would be attending in a few days. Connor was one of four young alums (and also Columbia students) chosen to keep an eye on the school's newest student. Each was chosen for a different reason, Connor was chosen for his personality and being a former member of St. Jude's soccer and lacrosse teams, two of the sports the Boston native was skilled in.

Kennedy looked out the window for several moments before deciding to head out. He still felt guilty for turning down Connor's offer but he didn't want to intrude. Connor was very busy as it was before taking on the "babysitting gig," so Kennedy felt bad at the thought of pulling away his friend from his family even more. The teen hated feeling like a burden and that was exactly how all of them made him feel to an extent… well for the most part.

He was snapped out of his thoughts by the sound of his phone. Kennedy picked it up and opened the text message.

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Just made it with a few minutes to spare, Mom.

-C

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He could only smirk at Connor's text. The blonde was definitely his favorite of the four. The other three looked at him for the most part as if he was a chore, but Connor acted like a big brother… a goofy but well-meaning big brother. It was touch and go first, but the two quickly hit it off and the "babysitting" became more bonding than anything else.

Kennedy made a quick reply. He wouldn't be a hypocrite after all.

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No texting during class mister!

-K

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Kennedy didn't wait for a response. He quickly pocketed his phone as he grabbed a coat and his keys. It was pretty cool for the early September day. While it wasn't much to many, his apartment felt like home. And for the first time in a long time, Kennedy was at home.

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Connor Windsor spotted pining like a middle school girl. What has made St. Jude's former heartthrob so down? Break up with a summer Columbia fling? You've been under the radar with your summer classes, but I've set my sites on you once more. What's your connection to Mystery Boy? And what kind of trouble have you and your abs been up to?

XOXO, Gossip Girl

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Connor Windsor is you average Upper East Sider: handsome, wealthy, athletic, and determined. The only child of the infamous "Windsor Design Duo," Connor was a star player on various teams throughout his childhood, but most notably shining on soccer and lacrosse in particular for St. Jude's. It was difficult to juggle training and playing for those two sports, but he made it work. He was a WINdsor and giving up was not part of his vocabulary, but then again neither was failure.

The blonde was often compared to his peers, but the comparisons were usually flattering. However recently another name came up in their circles: Nate Archibald. Though there were few similarities, the comparisons continued on. Outside of their common sports interests, they two had very different personalities. Whereas Nate was a frequent substance user, Connor was squeaky clean… or at least he came off as being so to his parents and peers.

Nate Archibald barely passed while Connor Windsor excelled in most areas without much effort, often with honors. The Windsor's were hands on and compassionate while the Archibald's were much more distant and indifferent, even bordering on cold and detached but unafraid of shoving their power and wealth around when needed to solve a problem. Connor earned his spot on the team, while Nate inherited his captaincy by process of elimination.

While Nate made friends easily, Connor was far more reserved despite his often goofy demeanor. One went with the flow and stuck to their clique while the other went wherever he was dragged. The differences go on and on, but it should be quite obvious now as to why he was angered whenever they were compared on Gossip Girl. Connor had worked hard to get where he was, but time and time again a blast would compare him to the elusive N.

"Not another one," Connor said looking at his phone. "I don't have time for this."

For the first year of college he had continued his familiar lifestyle: sports, studying, and sex. But soon he was partying in every sense of the word, not enough to get him out the team, but enough for his grades to slip. Like many Upper East Siders, the transition from free reign in a regimented high school to a much more fluid schedule with more demands is quite terrorizing to one's work ethic. But fortunately for the blonde, he soon learned that Columbia was nothing like St. Jude's and that he needed to start cleaning up his act or he would soon find himself kicked out and the laughing stock of his family, the team, and on Gossip Girl, though her followers tended to be more of the high school variety. Occasionally a former student would make it to the front page, but the good stuff was almost always exclusively about current students.

So when he got the chance to do something he did. That is how an only child became a big brother to a complete stranger. Well that was not his intention. He initially he thought of it as community service to work off all of the crap he pulled over the course of the previous school year, but within days it became exactly what he needed. It was definitely weird at first, but he wouldn't trade it for anything now. He became aware at the end of June and was thrown in the thick of it by July. By August he had a set routine and felt completely grounded once more, but in a good way.

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"So Windsor any plans tomorrow night?" a random red headed female said twirling her hair.

"About that Candace, I actually do. Sorry," he said with an awkward yet genuine smile.  
"I have to do something for my parents."

"That's too bad, it's been a while since we've been together." A flip of her hair and he was in her trap once more.

"How about tonight?" Connor was instantly caught—hook, line, and sinker.

"I'll see if I can move a few things around."

"Call me if you do," he said with a smile as he walked out of the emptying auditorium, leaving the stunned female in his wake. He knew he fell victim quite often so he was bright enough to serve them some just desserts after waking up each time.

"Are you sure that was smart?" a male voice said as he caught up to Connor.

Connor turned

"Roger, I do what I can."

"I didn't know you and Candace…" Roger wiggled his eyebrows to emphasize his point.

"Not really, we're just friends. I haven't had the time to even think about taking the next step, but we've caught a few movies together if you really have to know... Nothing recently but we do know each other from outside of classes... and when I have time."

"You've been blowing me off a lot too lately," the now identified Roger added irritated.

"I know man… I'm free for the rest of the afternoon if you've got time."

"I have to run to my next class but how about coffee in an hour?"

"Sure thing. My treat bro, I owe you one." Connor sighed at the thought of money fleeing from his wallet. He knew it would be the first of many before Roger forgave him. "Have fun in Orgo!"

"Why couldn't you go with me? I could totally use your brains right now!"

"I don't want to be a doctor, so why subject myself to anything beyond the minimum requirements for science courses? Now hurry before you're late!"

"When did you become so responsible Connor?" Roger said shifting his weight. He was ready to go but really wanted to know what brought about this new change in his friend. Unfortunately there was no time.

"A few weeks ago," he smiled. Roger looked on with disbelief as Connor began walking away in the opposite direction.

'Did he meet someone else?' Roger thought to himself as he walked to class. He was truly dreading Organic Chemistry, but the thought of Connor feeding his caffeine habit made it slightly more tolerable.

On the other side of the building Connor whipped out his phone as he received a text. He didn't know whether to answer it or not, but erred on the side of caution. After all it could be his "brother."

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Who's turn is it again?

-Oliver

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Connor could only laugh. Leave it to Oliver it to forget the rotation. Of the four, he was the one so focused on his sport, and nothing else, that it bordered on complete obsession. His teammates called him a complete nightmare. One even dubbed him a certain term referring to certain German military officers, but even that didn't really do him justice. He was nice enough, but he was definitely intense. It still amazed anyone who met him that he could schedule his life around his favorite pastime but forget every part of the schedule other than when he was practicing, working out, or playing.

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Mason and then mine. Enjoy your weekend!

-Connor

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You too dude!

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Connor could only chuckle as he imagined Oliver reading his text in person. This whole experience was good for each of them, and none of them knew it yet. It was simply too soon into the experiment for the results to become blatantly obvious enough to the subjects.

While he had his phone out he dialed a familiar number. He sat on a nearby chair as he waiting for the person on the other end to pick u[.

"Connor honey everything ok?" asked a female voice.

"Everything's fine Mom..." He paused for a second. "So I have a bit of a problem."

A long sigh came from the other end. "I take it he said no."

"Yeah…" The blonde's exasperated tone did little to faze his mother.

"It will work out. Don't press it too much. Things happen for a reason honey."

"I don't really have time for this."

"You're doing better than where you were last year already. Just give it time."

"You think?"

"I know."

"Thanks Mom."

"That's what moms are for." Connor imagined his mother saying it in person while cooking with a frilly apron… Sometimes his imagination got the better of him, especially when it involved daydreams of his mother cooking, as if that would ever happen. Baking maybe if he was lucky, but cooking was a no go.

"Now make sure you become his rock. I'm sure we'll be meeting him very soon. We still have plenty of time."

"Maybe…"

"Connor Andrew!"

"Fine, he will.

"Now that's much better. Be a dear and call your father. He has some other things he wants to go over with you."

"Ok."

"See you then."

*click*

Connor dialed another number and tapped his brown leather shoes on the tile of the lecture hall's floor as he waited for the person on the other end of the line to pick up his call. The clicking of his heels formed a rhythmic beat as he waited—it quickly took on the tune of his latest favorite song..

"Kyle Windsor."

"Dad, it's Connor."

"What do you need Sport?"

"Mom told me to call you."

"Oh…" Kyle said knowing exactly where this was going. "Well it's imperative that you convince him to come meet us. I have pulled some strings and our calendars have aligned so this needs to happen this weekend."

"I'll do my best." The blonde slumped into the chair upon which he was seated as he mentally groaned. This was one nasty situation he was not getting out. He was stuck proceeding with it.

"That's the spirit Sport!" Mr. Windsor's tone made it difficult for his son to determine was that statement was meant to be encouraging or sarcastic.

"He's really nice."

"I'm sure that he is. We can wait to meet him in person. If it doesn't happen this weekend, it can happen again, but we should get this over with ASAP. School is right around the corner for him."

Connor heard some talking in the background.

"Sport, I've got to go. We're having a meeting right now. I'll see you at the Cabin."

"Cabin?"

"Yeah, I think it would be better."

"It's a heck of a drive, but if you say so."

"I know."

"Bye."

*click*

Connor let out a sigh and looked at his Rolex. Despite all of the texting and phone calls that he had made, the blonde still had some time to kill before he was supposed to meet Roger for coffee. He decided he'll kill some time by texting some more.

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Mason?

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Connor…

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Connor sighed. Mason was so, well formal and irritable, such a horrible combination in a 'co-worker.' Their different habits weren't enough to get under each others skin, however their personalities did clash.

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I might be taking Kennedy with me this weekend to see the 'rents. I know how much it would mean to them and him.

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Really?

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Yeah. I know you had plans and the others didn't want to watch him. I'm free anyways.

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Thanks man. But how likely? I really can't afford being unprepared. Can't catch a curve ball. Never have, never will.

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Connor smiled at Mason's baseball reference. Then again each of the four managed to allude to their past times in their conversations some way or another.

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I hate to say this Mason, but as soon as Gossip Girl makes her move you'll be free.

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Why?

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Several attractive and unattached St. Jude's alumni being seen in his company regularly… Us being two of them, Mason. She has been far too focused on him.

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You're right.

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Worse to worse I'll guilt him.

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Lol… I've got to go. Thanks again man.

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No prob.

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Connor put away his phone as he headed for the closest Starbucks to meet Roger. He desperately needed coffee after all of those conversations. He loved Kennedy like an annoying little brother, but there was just so much emotional commitment involved. It was beginning to put a damper on his social life or at least that was what he kept telling himself. In truth he found himself happier guiding his "little brother" along, making sure he didn't make the same mistakes he did.

He began texting Kennedy while waiting for Roger, hoping all was going well on the other end. But in reality nothing was.

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Hope you enjoyed your first glimpses at our protagonist and some of my original characters. It's going to be slow going for a while before it begins to pick up. Hopefully there aren't too many typos. That's one area I still need to improve on after all these years.

-Griff


	3. Should've Said No

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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Spotted, N and C with our new Mystery Boy. Sources say C has a past with him. I wonder what kind of past C could have with someone like that? Mystery Boy doesn't seem like much, but then again this city is full of surprises. How will N deal with having to share C? Tune in and see what other secrets Mystery Boy is hiding. I can't wait for it all to come crashing down.

XOXO, Gossip Girl

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Kennedy walked around the city for a bit to better familiarize himself with the area. It wasn't exactly like he had anywhere to be today or anything to do other than a few errands he could have done the following day. Far too punctual for his own good, the teen ventured around the city that never sleeps before he could even get the run down from one of his minders.

Everything was similar yet so different from Boston. It was bigger, shinier, and a lot nosier. However all of the quaint reminders of home such as the nonsensically shaped roads and historic architecture was replaced by precison and function in the perfectly aligned blocks. Despite all of this, it was quickly feeling like home, so much that Kennedy walked right into someone else without even realizing it as he was so deep in thought.

"Watch where you're going next time idiot," a snarky yet familiar voice said snapping Kennedy out of his thought as he immediately realized what he had done... Well to be honest the throbbing pain of smacking foreheads with someone may have more to do with that than hearing THAT voice.

Kennedy knew that voice somehow. He couldn't put his finger on it at first, but Sometime long ago he had heard that voice and he couldn't quite place it at first, but after a few seconds he got it. He blinked several times to make sure he was correct in his assumption. Puberty had not been to kind to his friend.

"Sorry… wait Charlie?" Kennedy asked. He knew he was taking a bit of a chance, but his gut was telling him that he knew this stranger. Sure the clothes, hair, and just about everything else was different from the last time he had seen the other male, but there was the same mischevious undertone present even when being yelled out.

"Wh… Kennedy?" the surprised form of Chuck Bass replied before he had fully processed things. If his mouth could have hung any more open it would have been at his feet. This was certainly something neither was expecting! Normally both males would have blown up in expletives, but that all went out the window when they finally recognized each other.

The two stood there on the sidewalk looking at each other in awkward silence. They sized each other up and took notice of the changes puberty had brought them respectively. Away from the place from where they had met, the two were quite different from the last time they had seen each other.

"What are you doing here? Shouldn't you be in Boston doing whatever you peons do?"

"I would be if someone didn't bring me here," he said with a far away look. "Trust me I wouldn't be here if I didn't have to. I'm a Boston boy at heart, but I could get used to being a New Yorker…"

"What's that supposed to mean? Don't tell me…"

"No. No. NO!" Kennedy blushed at the implication, or at least what he thought Chuck was thinking that he was implying. "Apparently my parents left me bit of a fund for my education expenses to attend a good prep school on the Upper East Side. Or at least that's the story that the folk's at St. Jude's is telling me… I havent really found much online, but it seems ok... Kind of pricy too, but I'm all taken care of for tuition and someone else is paying for my other expenses for now at least." Kennedy's eyes darted off as he said the last part in a hushed tone, trying not to let his embarrassment show that he was a charity case. "It doesn't really make much sense to me at all, but I'll be in your neck of the woods for the time being on someone else's dime."

"Well now isn't that the predicament? Your life just got an upgrade." Chuck said in a not so mocking tone. He knew that his old friend was not saying something, but now was not the time to press further. "I just so happen to go to St. Jude's."

"It's weird… You've changed a lot since the last time I saw you Charlie." The playboy swatted away the hand the Bostonian attempted to use to touch the playboy's precious locks. Friend or not, no one touched Chuck Bass' hair unless they were wrestling beneath the sheets and most definitely female...

Kennedy's smile did something to Chuck's stomach that he couldn't place. He had not felt this way in many years and it completely unnerved him. He liked to remain in control and the Boston native had usurped the control from the beginning of their chance encounter and it was becoming blatantly clear who the alpha male was here despite their exteriors and postures.

The two were interrupted before they could say anything else. Sometimes in a city so big you're allowed to have your own private bubble in the middle of chaos. And in other cases you don't get to have such a luxury.

"Chuck, what are you doing here? You were supposed to meet me ten minutes ago," said a certain flaxen haired pretty boy with bangs.

Chuck ignored Kennedy's statement and introduced his two friends to each other.

'Now I can turn the tables,' he thought to himself as he mentally grinned a wicked smile. He couldn't do it externally or his two friends would know he was up to something. After all he was a schemer no matter where he was.

"Nathaniel this is Kennedy, an old 'friend.' Kennedy meet my good friend Nathaniel."

Nate failed to notice Chuck's emphasis on friend when describing Kennedy. This would be something he would later realized upon further reflection. The Upper East Side athlete looked at Kennedy with an inquisitive look trying to imagine how exactly those two individuals could ever be "friends."

They looked like they were from two different worlds, and sure as heck acted like it as well! Yet here Chuck was talking up with the same kind of person he talked poorly of day in and day out. Sure the new teen was dressed far more casually than Chuck, but the brunette was of the same callibur as the wannabe surfer boy. And then it hit Nate what kind of friend Kennedy could be.

"Chuck…" Nate began in a judgmental tone only to be cut off before something stupid could escape his lips..

"Not that kind of friend Nathaniel," Chuck emphasized, immediately quashing Nate's presumption or what he assumed was the other male's assumption.

Kennedy could only mentally smirk. Charlie had definitely changed. And apparently his friend wasn't the brightest light bulb on the Empire State Building.

"Oh… Call me Nate," the golden boy said offering his hand, which Kennedy returned with a firm, yet crushing grip to reinforce what kind of friend he was and what kind of friend he definitely wasn't.

"It looks like my dear friend will attending school with us this year Nathaniel. I'm sure you'll get along well with your similar interest. In fact I can tell this will just be the beginning for us. It's so great to have another mind to corrupt and do my homework for me, Kennedy. Still a genius?"

Nate rolled his eyes at the use of his full name. Both teens looked at Chuck confused, to which they received no response. Nate didn't understand where the whole school thing related to their conversation as it came out of left field. On the other hand Kennedy had no clue why Chuck was corrupting people or having them do his homework for him... Sure there was that one time, but still...

"That's pretty cool! Why don't you join us Kennedy? We were about to meet up for lunch and I'm sure they wouldn't mind adding another seat to our reservation. We're frequent regulars and our families have been dining there for years."

Kennedy blushed… "I'd hate to intrude. I have a lot of things to get done today."

Chuck chuckled. "Give up Kennedy, its only lunch. You'll have plenty of time to do whatever you need to do later. Summer reading and school shopping you can do anytime. Lunch with us is simply something you don't pass up on." A pause was made as Chuck felt his phone vibrate. "It will be a good way for us to get reacquainted even if you choose to dress like Nathaniel. Though I fear it will be pointless as Nathaniel always gets his way."

'Is that supposed to be a good or bad thing?.' The teen let out a mental sigh as he was trapped like a rodent. 'Why do I have the sudden distinct feeling that there was something I am not catching on to?' Kennedy thought to himself as he put up a front.

"Fine, I'd be happy to join you to," Kennedy said in a fake voice. He didn't know whether he liked Nate or not. While Archibald wasn't the smartest person in the world, he was nice and quite good looking. However he didn't want a stranger, even if they were a friend of a friend to learn of his past so soon.

"Awesome!" Nate replied equally as enthusiastic. "I'm starved."

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Kennedy followed the two as the trio walked for a minute or two to their destination. Immediately he could only groan about the cost of everything and the sudden feeling of being seriously under dressed by the mere presence of the building the restaurant was located in. He found it relatively easygoing… Sure Charlie or rather Chuck was not the same person he had met years ago, but it didn't phase him. Thankfully Nate was even more so underdressed than himself or the teen would have been even more stressed. After placing their orders Kennedy excused himself to use the restroom while Nate began to interrogate Chuck on who this "friend" truly was.

"Who is he really Chuck?" Nate asked.

"A friend."

"Friend?"

"Nothing more and nothing less. Is it so hard to believe?"

"Actually yes Chuck… You beat on all of the other kids on scholarships, but you let Kennedy in with open arms?" Nate continued. "He doesn't exactly look like the high society kids you typically surround yourself with."

Chuck raised an eyebrow.

"You know what I mean CHUCK... People like us." This was an odd thing for Nate to say, but he meant it. Chuck spent money like it was going out of style and ensured he associated himself with equally fabulous and wealthy individuals. He had no time for the poor. Yet he pulled a random middle class teen off the street and Nate was just supposed to accept it? Nope, the blonder teen was not going to drop this and let his friend off the hook, though he didn't have much to stand on at the moment as even the casually dressed Kennedy looked more formally attired than himself.

Chuck was careful with how he responded. While he disliked a certain Humphrey in particular, this situation was beginning to make him look like a hypocrite and he didn't need that. His brunette friend was special and looks were very misleading in this case. He had to make this painfully clear before Nate became another one to fall for the facade Kennedy put up as the under the radar, average Joe.

"Kennedy's from Boston. And before you ask, his past is his own to tell… Tragic actually to be honest." Nate gave Chuck an odd look which he ignored immediately. "Don't go digging Nathaniel as that won't help you at all. And besides Humphrey is from Brooklyn. Boston is a much nicer place."

Nate furrowed his eyebrows as he remained silent as he couldn't believe where this conversation was heading and he had been friends with the other male practically since birth..

"...Much hotter girls too. The brainy ones are always wild in bed and Boston's the college town."

Nate laughed at Chuck's response… Maybe there really wasn't anything to be worried about after all.

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Kennedy splashed his face as he looked into the mirror. Connor was right, things were VERY different from his life in Boston. Apparently his friend Charlie was now going by the name Chuck and he along with his group of friends were the subject of many Gossip Girl blasts. It didn't take a genius for one to realize Nate was the infamous N. The mysterious blogger's numerous posts did the other teen little justice as Nate appeared to be much nicer and less self-centered than he had read online.

The black haired teen felt very out of place in the restaurant. While he had been provided with new clothing and everything else courtesy of his mysterious benefactor, he still felt odd being here. He no longer felt comfortable in his own skin. He barely recognized himself nowadays… He was just glad that he had taken Connor's advice and started dressing "properly" or it would have been even more awkward, with or without Nate walking in a gray sweatshirt, black sweat pants, and red Nike sneakers.

"Stupid blonde," Kennedy mumbled to himself as he received and read a text from said blonde minder of his.

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Be careful what you do… Gossip Girl has set her claws on you. Nice place for lunch. A little fancy though even for me. -C

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Kennedy sighed… He didn't personally follow Gossip Girl like everyone else did but Connor did open his eyes to that particularly socially devastating source of malevolence and all it took was a few hours to see how one tip could lead to a life time of disaster. He knew that he had rotten luck, but Kennedy didn't expect this.

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I'll try. Apparently the plot thickens. Is it too late to take up your offer? I need to get away. -K

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Our Boston native waited impatiently for a response in the restroom blissfully unaware someone was watching him from one of the stalls.

Kennedy's phone rang signaling Connor's response.

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I knew you'd come around. The 'rents will be thrilled. We WILL talk later about logistics.

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Kennedy sighed as he put his phone away and opened the door, completely ignorant of the individual in the stall. Thankfully our friend was texting and not talking to his minder or things could have taken a much more drastic turn for the worst. The texting and comment about a "stupid blonde" were hardly enough for Gossip Girl to build upon thankfully… well at least for now.

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Kennedy returned to hear the tail of end of Nate and Chuck's conversation. Thankfully he walked slower than he normally did. It was nice to know that deep down underneath Chuck's sadistic exterior, the caring Charlie still existed.

"Sorry, had to take a call," Kennedy lied as he slid into his chair. Immediately he noticed that their food had already arrived and the duo had waited for him to begin eating.

"Don't worry about it," Chuck added. "I'm sure it was well worth wasting our time." Exteriors had changed but Chuck was still Charlie. The food was still giving off steam so it was quite obvious it hadn't been placed down for more than a few moments.

"Be nice Chuck, he is your friend" Nate said before turning his attention to the other brunette male. "So Kennedy, how do you know Chuck? I've grown up with him and he's never mentioned you."

Kennedy hesitatedas he came up with a believable tale that didn't give away too much. He needed to have something that worked for both Charlie and his new Chuck persona. He was used to thinking on his feet but this was kind of ridiculous. A few moments later the words began escaping his lips before he even noticed.

"I met him a good few years ago. Well before Chuck as you know him existed. 'Charlie' arrived right around the time I just happened to really need a friend." He turned his head down and away a bit as he finished. He couldn't look at Chuck in the eye saying it. Now was not the time to elaborate further. "We lost track of each other after a while, but apparently the fates didn't want that injustice to last any longer."

Chuck didn't let Nate reply to that. There was no chance he was letting the pretty boy shove his foot in his mouth a second time. A subtle kick to the shin worked wonders with Archibald, something out favorite Basstard had picked up from a certain brunette mean girl.

'Looks like I rubbed off more on you than you thought,' Chuck thought to himself. 'My first success story.'

After some more awkward conversation to topic of school came up.

"Chuck mentioned earlier you're going to school with us this year," Nate said trying to rid the air of the awkward silence. "Are you sure you want to put up with him?"

"Yeah… I'll be going to St. Jude's with you two. I'm more than capable of handling him Nate. It's you who should be worried." The sinister smile that crept up on Kennedy's face did its work.

'I feel like a proud parent right now,' the sharpest dresser of the table thought at he observed the verbal war between his friends.

'Let's see how you work your way out of this Nate,' Nate thought to himself as he waited for Kennedy to continue. There was no way he was going to screw up again so soon. He could already imagine how Chuck would go off on him later.

"Apparently my parents set up something for me years ago before they died." Kennedy looked down as the two Upper East Siders had identical looks of shock and horror on their faces.

'So much for a nice lunch,' Nate thought as he immediately felt guilty that he brought the subject up at all.

"You just had to beat further upon a dead horse didn't you Nathaniel?" Chuck said in a very out of character moment.

"Don't worry about it Nate. There was no way you would know." A wave of relief crashed upon the picture perfect jock as he let out a sigh of relief.

Then Kennedy turned to the other participant of the lunch with an interesting look upon his face. "Chill Charlie he was only asking question. How was he supposed to know?" Kennedy's new smile removed much of the tension. "However you did know some of this so you should have stopped him before we got to this. But what has happened is now behind us. Why don't we just try to enjoy the rest of the meal?"

Kennedy cut into his fillet as the other teens could only be reminded of another teen. Instead of Nate feeling reprimanded like expected, it was actually Chuck who received the brunt of the cold shoulder. The trio ate in silence before the newcomer took it upon himself to set things back on course.

"To be honest I'm just happy to know they cared enough to send me to such a great school." Kennedy continued the conversation soon after as it was quite obvious the other males would not drop it despite their upbringings. "And while I appreciate the gesture, I have to wonder why I'm only getting my acceptance now as junior? I could have used some of this money growing up instead. My last school blew and I had to carry my whole team literally."

Neither of the Upper East Siders knew how to reply to that. It was quite strange to have a transfer so late in the game, but it wasn't unheard of. There were definite holes in Kennedy's story and Chuck didn't know whether they were intentional or not.

'Looks like I'll be having to hire an investigator again…' Chuck thought to himself as he cut through his steak.

"So you'll be taking classes with us then. If you're anything like Chuck, I'm sure you must hate everything that isn't either illegal or involving the other sex." Nate's attempt at lightening the mood had the opposite effect and felt like a slap on the face for the other two, not that they would ever admit it. Chuck took it with grace and smirked before he and Nate waited for a response. Mind games were powerful and were also a necessary evil.

"Actually, I played lacrosse back home… and soccer. But then again I did a bit of everything to be honest, but mainly those two. "

"Really?" Nate replied interested. "I guess then I'm going to have to convince you to try out then seeing as I'm the lacrosse team captain."

"We'll see Nate." Kennedy continued eating his salmon. He was blissfully unaware how Nate and Chuck were hanging onto every word he spoke. "If I have time on my plate then maybe, but I don't really know what I'm getting myself into after all," Kennedy said with a laugh that set both Chuck and Nate on edge. The last comment was true. He really didn't know what kind of scenarios he was going to get into.

It wasn't a fake laugh, but something was kind of haunting about it. It spoke true to his past as well as working into his plan.

Suddenly there was a ringing noise. It turned out to be Nate's phone. He looked at the screen before his face turned solemn. A polite yet forced smile graced his handsome face as he addressed his fellow diners.

"Blair is expecting me Chuck. I've got to go now," Nate said as Chuck acknowledged it with a nod.

"Don't keep her waiting."

"I won't," Nate replied before turning to Kennedy. "It was nice meeting you Kennedy. If you have any questions feel free to shoot me a text. I could always use someone else to practice lacrosse with."

"Sure," Kennedy said as Nate left.

Chuck waited a few moments before speaking.

"Nathaniel is a great boy, but he isn't the brightest. His girlfriend Blair is… intense. Stay out of her way and you will be fine Kennedy."

"I will."

"You should take him up on his offer. It would be a good way for you to fit in quicker and look good for college. Nate's quite the popular guy."

"Maybe… I just have no clue how long this is going to last Charlie. Sometimes I feel like this is one big sick joke."

"Don't worry Kennedy," Chuck said after he signed the bill before the other teen could even fight for it. "I may not have been there for you in the past, but I'm here now starting with this lunch. Next time I'll work on your wardrobe. Nathaniel may be able to get away with that but we both know you have better taste and more brains than him."

"Thanks Charlie!" Kennedy said with a smile that flustered the normally collected and sharp witted Chuck.

"While around my friends, would you mind calling me Chuck?"

"Errr sure Chuck."

"You can call me Charlie in private… I have an image that I need to defend."

"Ok." Kennedy didn't know exactly how to respond to that. There was something being implied that he didn't like.

"Why don't you come back to my penthouse, we have a lot of catching up to do."

Kennedy sighed as he looked at the time on his watch. "It's not like I have anything better to do. All of the places I needed to visit today are all closed now."

"Wonderful. Don't make it sound like torture."

"I don't think I know you any more Chuck."

"I don't think you ever did," Chuck replied as the two got up and exited the restaurant.

"You might be right, as I never expected for you to be one worried about college," Kennedy said innocently. "I thought college was for suckers?"

Chuck stopped walking for a moment before moving once more. It did not go unnoticed by our Boston friend.

"You're not the only one who remembers Chuck. I guess there is a bit of Charlie underneath that well dressed exterior after all. No matter how much you try to bury him, there will always be that little boy that befriended me by the sea."

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Nate was quite surprised to see a new blast as he rode to meet Blair. From the contents, he could only imagine what his girlfriend would try to extract from him. After all Blair Waldorf did not like surprises. She like always remaining in control.

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Spotted. Mystery Boy having lunch with N and C, but only for N to bail on them for B I assume. Mystery Boy got into a car with C not long after. I need details gentlemen.

XOXO, Gossip Girl

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Kennedy had a hard time still getting used to the new lifestyle. He wasn't used to all of this wealth and extravagance even after his introduction via his friend Connor and other three, not that they were very much fun. Getting used to the new side of his childhood friend was even weirder… After all these years he never imagined that he would run into Charlie again… and yet here he was in Chuck's penthouse about to drink a bottle of some god knows how expensive alcohol.

"You never told me you were from New York Charlie."

"What's your poison?" Chuck replied changing the subject immediately. He was not in the mood for small talk. He had considered including the makeover today, but then he was reminded of a certain frightening fashionist and instead decided upon his old standby.

"Tequila," Kennedy replied nervously as his question was quickly left unacknowledged and unanswered. He wasn't a big drinker but apparently his friend was. It's been a while since any had touched his lips, but Kennedy was ready for some to quench his thirst. He knew saying something like rum or vodka would earn the disdain of his apparently well versed drinker of a friend so he said the first thing that came to mind that he wouldnt puke up after a few shots and was also popular enough not to raise eyebrows.

"Don't worry I won't get you too drunk. Your secrets are your own after all," Chuck said as he picked up a bottle and two shot glasses. "Can't have you gushing your heart like a cheap hooker on our first night together."

Chuck's smile was still the same whether he was Chuck or Charlie. Maybe they weren't too different after all. Were they two sides to the same coin or was it just growing up?

Maybe it was childhood innocence, or maybe it was nostalgia, but Kennedy obeyed Chuck without much thought.

"Well… things went downhill really fast after you left to be honest."

Kennedy didn't look anywhere in particular when he said that as he had no intention of laying the guilt upon his friend.

Chuck immediately downed one of the shots he was pouring as he heard that. Something in that statement felt like a cheap shot to the stomach.

"Don't blame yourself… It's not like you were responsible." Kennedy didn't really know what to say. He had not seen his friend in many years and was beginning to wonder if they ever knew each other at all. "You wouldn't have been able to stay anyway. This was before cell phones and neither of us were smart enough to give full names."

"I… I…" Chuck tried to respond but didn't know what to say. He was so used to his tough exterior that he didn't know how to really express his true emotions to any one.

"It was hard you know… You were my first real friend. And then everything changed… Did you know I was an orphan by the time I was ten?" Kennedy said throwing back a shot before quickly pouring himself another as Chuck blinked. "They were all gone by then and things never seemed to get better... And if they did they only got worse."

"Kennedy…"

"No parents, no siblings, nobody… The funny thing is that I couldn't find a trace of them anywhere… It's like they never existed."

Kennedy looked at the crystal shot glass with great detail. "There were no distant relatives on file or anything. I was all alone… And then I opened up when met you, only for you to leave me as well."

Chuck did something very out of character, he pulled the bottle of alcohol away from his friend and moved close to his friend on the couch.

"Well I'm here now." For once in his life Chuck sensed that someone was vulnerable and did not take advantage of it. Well not that he could… he had standards after all. And no matter what he wasn't crossing that line, even if he had dabbled with his own sex here and there. Kennedy was both a friend and also far too clean cut for such a rendevouz. "I won't disappear this time."

"I'm glad you are here Charlie and I will hold you to it. A friendly face in a brand new city is exactly what I need right now... and a bottomless bank account."

Chuck recognized that face.

"I don't know how much longer I could last," Kennedy said in a sleepy voice with double meaning to his words as he put his glass down on the coffee table before him. "It's just so hard sometimes. And now I'm all alone in a new city…"

Not long after Kennedy passed out from the alcohol and his head landed promptly in Chuck's lap. The Bass heir just sat there thinking for a while. He often complained that his life was fucked up, yet he had just been reunited with a childhood friend who had it much worse than him. Chuck just sat there like that with Kennedy thinking. Sometimes he wished his father was dead, but now he realized how horrible a statement like that could be. He had a father and an infinite seeming supply of cash at his disposal. Kennedy had known of that, yet he retained the spirit that drew him to befriend the Boston native those many years ago.

"You'll never be alone again," Chuck said to himself as he just sat there.

If it were anyone else, he may have taken advantage of the situation or used his silver tongue against them, but Chuck didn't know how to react to dealing with someone even more broken than himself. His family life was that of a run of a mill soap opera, but Kennedy's was of an Oscar winning movie. There's always a parent that is distant or uncaring, but rarely there is someone who does not have anyone to call family.

Careful not to wake his friend, Chuck reached for a shot and let the tequila burn down his throat before pouring another. He sat there in silence looking out the window as night fell. Oddly complacent with the way things were.

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Kennedy awoke hours later to find himself alone on the couch with a blanket draped over him and a pillow beneath his head where his friends lap lay only hours before. It took a few moments for him to recall the events that had transpired.

'I wonder how Chuck maneuvered himself out from under my head… I'm a light sleeper and this pillow wasn't even in this room!'

Along with the alcohol-induced headache, the pain of realizing what he said to Chuck hit him in the stomach… He acted like a jerk with the way he had worded things… Here he was reunited with an old friend and dumps his problems on Chuck as if all of it were his fault. None of it was Chuck's fault to be honest but at the time he felt some vindication in displacing some of his anger at his friend.

Kennedy checked his phone to see the time and that he had a few missed texts.

It was three in the morning and he assumed Chuck was asleep.

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Hope you had a fun day. -C

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I'm going to be heading over to check in on you in a bit. Let me know if you need anything Kennedy. -Mason

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Stopped by and you didn't respond. Connor said you were heading out to explore the city, you ok? It's not like you to not pick up. -Mason

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Just got a text from Mason saying you didn't check in with him. You better be getting lucky if you're ignoring us K. I'll cover for you, but you have a lot of explaining to do. -C

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Kennedy, just got a text from Connor. Let me know if you need anything. Feel better dude :D -Mason

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You owe me, like cleat cleaning for a month owing me. Bro you so are going to regret whatever or whomever you're doing when I'm through with you Mr. -C

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Kennedy couldn't help but smile. It was so Connor to make everything lacrosse or soccer related… In fact Connor wasn't the only one with quirks. Each of his four "caretakers" were all so different but they all came together to keep an eye on him. One or two them were simply doing it for the extra money and nothing less, but Mason and Conner were definitely the more friendly ones…

Not that Mason was super friendly either… There was a reason Conner was his primary caretaker after all, though he wasn't sure if he truly made that decision himself as the blonde went on and on about how he always wanted a little brother to impart his wisdom on. But despite their motives, Kennedy welcomed their company. It was kind of cool to him to suddenly have four brothers—each very distinctly different from the others, but all intently focused on his well being.

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I'm not having sex! I'm not you :p I have standards. -K

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You could only dream of being as sexy as me! Have fun and be safe tonight bro. -C

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You're such a ham. I'm with a friend. Not that kind of friend. You're right. I'm not you. Or into you :p -K

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Connor didn't respond any further and Kennedy was glad for it. Texting while still slightly intoxicated in a dark room was definitely doing a number on him. Our Boston friend wandered around the penthouse looking for his friend. But he had no luck in doing so. The place was eerily quiet. It looked so different at night. Now that he thought about it, it was so like Chuck to leave him unannounced…

As he continued his search, Kennedy found that there was no one in any of the beds, though there were male and female garments strewn about the rooms that definitely did not belong to his childhood friend.

'Equal opportunity indeed,' Kennedy chuckled as he made his way to the kitchen. So he did the next best thing he could think of on short notice, he left a note on a piece of fancy paper he found laying about on the counter.

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Chuck,

Thanks for everything.

Heading home. Have plans tomorrow.

Will be in contact soon.

-Kennedy

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Sure he could have texted him, but Kennedy thought a note was well a little more personal and more in tune with his person. He personally preferred leaving thought and concern in everything he did. Not to mention he didn't want to wake or interrupt his friend wherever he was. They had exchanged numbers on the ride over, but this was not the time to test the waters. In fact Chuck had taken it upon himself to program several other numbers in there as well, not that Kennedy could put a face to any of them beyond Nate's entry.

It was going to be a bit of a hike in his slightly inebriated state, but Kennedy longed for the comfort of his own bed. Not to mention Connor would kill him if he wasn't there for the next check in which would be a self-imposed one tomorrow morning. And for some reason the thought of hailing a taxi never crossed his mind.

'Hopefully he brings coffee,' he thought with a bleak smile as the chill of the cool air hit him head on.

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On his way home he saw an oddly familiar looking older man walking down an alley with a shifty looking character. In his normal state, he may have investigated it or even been able to recall how he recognized the man, but he was too cold and tired to say there and investigate. This was New York after all and drug deals were constantly going down across the city as well as other shady transactions. He was not in the mood to get mugged or murdered before he got to the bottom of his personal mystery after all.

Who was he to get in the way of stimulating people and the American economy? While illegal, he would be a hypocrite if he interrupted. Rather, Kennedy kept his eyes on the prize and used the image of his warm bed as he continued to walk back to his apartment. It wasn't a crazy distance, but being tired and slightly buzzed makes anything much longer and taxing.

There was one thing about it all that bothered him however. He had no idea why that face seemed familiar or where he had seen it before.

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Today started like any other day, but it had lots of twists and turns. In the end he made a new friend and reunited with another. Chuck proved today that Kennedy was correct in befriending him all those years ago.

Gossip Girl may have her claws in range for Kennedy, but so did someone else. Things were not so quiet on the Upper East Side front. And that was exactly how we like it.

Secrets can only remain hidden for so long…

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Mystery Boy seen leaving The Palace alone in the middle of the night? Is there something less than wholesome going on there? I didn't know you had it in you C! I'll get to the bottom of it. I always do. Watch out Mystery Boy as C is quite the bad boy. You want to make the right kind of friends here.

XOXO, Gossip Girl

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Hope you're watching all the drama unfold. All feedback is welcome. Your reviews can only help make this better.

-Griff


	4. Holy Ground Part 1

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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Spotted. Mystery Boy. He isn't much of a mystery anymore. Though a lot of details are still missing to even me. Looks like several of St. Jude's more handsome students and alum's have been in his company. First C and N, now this? Why do I have a feeling that this will end in shirts vs. skins? I'll root for your Harem of Hotties any day K. Just name the time and the place and your team will have a legion of followers.

Sign me up!

XOXO, Gossip Girl

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Kennedy slept away as much of Friday as he could. School was starting on Monday. Connor and the others had already had a week of college classes under their belts. Tonight he would be meeting the Windsor's. It had been quite a while since he had touched alcohol, and Kennedy was really beginning to regret it.

'Charlie's always been a bad influence on me,' he thought to himself as he kicked himself out of his warm cocoon of Italian sheets and down pillows.

A quick glance at his alarm clock showed him that he still had some time before the impending meeting. A ring of his phone told him that he had a new message… And it was from Gossip Girl? Well it wasn't to him personally, but it did involve him unfortunately.

'I so don't need this right before school starts.' Kennedy discarded his phone as he gathered a fresh change of clothes. 'Why are they letting their lives be tormented by some jealous stalker/bully?'

He left his room for the bathroom only to remember that he had forgotten a towel. The sound of his ringtone chirping once more notified him of another incoming (text) message.

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Lay low this weekend. She'll have her next target soon enough -Charlie

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Kennedy could only smirk. Charlie was still in there after all these years. Beneath the expensive clothes and scathing words was the friend Kennedy could still recall from years ago. Sure the Chuck persona was a bit much, but he was beginning to see why his friend had changed the way that he had… So it took a bit of self-restraint to not include Charlie in the text despite Chuck using the nickname himself.

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Don't worry Chuck. Spending the weekend with one of my Minders. None of her followers will get a shot of me.

-Kennedy

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Our friend could only wait in anticipation of a response. It didn't take that long for it to happen. Kennedy picked at his fingernails in boredom while waiting. Sometimes he had the patience of a saint while he had the emotional span of a teaspoon at other times. Right now he was leaning more toward the latter.

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Minder? Is there something you're not telling me? And I told you before Charlie is fine when it's just us.

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Kennedy sighed as he typed a response.

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One of my 'babysitters.' Thats a story for another time... And now is a good time as ever to practicing calling you Chuck, Chuck.

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He could only image how Chuck would respond. Things were so different from the way they once were, but Chuck was still the same deep down. His façade may have been upgraded and tweaked beyond recognition, but the same insecure, adventurous, and closed off boy remained deep down in that shell of a womanizer somewhere.

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If you say so.

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The dark haired teen let out a big sigh. That response was far too short and the length was the least of his problems. This was really cutting into his shower time. So much for his shower right? Kennedy took a quick whiff of himself and made a funny face. He knew he desperately needed a shower stat but the question was how to wrap it up with Chuck quickly without being rude and cutting his friend off.

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Weren't you paying attention to me in the limo Chuck?

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Kind of… Was more glad to have you back to be honest.

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Kennedy smiled. It felt good to have the feeling being mutual. Chuck was much cooler than the warm Charlie he encountered years ago, but he was glad for the distance to be honest. Kennedy needed space and Chuck was going to do that to keep up his persona.

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Good to know. I have to run. But my minders are paid to make sure I check in and stay out of trouble. Basically glorified help.

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Chuck never texted back, so Kennedy took that as a sign of acknowledgement. The obligatory 'ok and have fun' was unnecessary and unwanted to be honest. The teen stripped off his remaining articles of clothing, threw them in the hamper, and turned on the shower. He looked at himself in the mirror noticing how much he had changed already. A new haircut, clearer skin, and whiter teeth were a few of the things

Kennedy still felt like he was walking on eggshells with all of these Upper East Siders, but he was beginning to get the hang of things. Or at least he hoped that he was… A weekend with Connor and his family was exactly what he needed. He just hoped to God that they weren't too WASPy. Connor seemed decent but you never know.

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Connor showed up at five o'clock exactly in a navy blue button down, powder blue tie, and navy slacks. Kennedy had spent a lot of time fussing with his hair and deciding on what to wear. He wanted to impress the older athlete's parents. The blonde hadn't mentioned much about his family to be honest, Kennedy wasn't sure whether it was to seem more down to earth or it completely slipped his mind. In fact Kennedy was going into the situation completely blind.

"Not going to try to back out now are you?" Connor said ruffling Kennedy's hair.

"Dude!"

"Sorry, but your hair looked too perfect." Connor laughed at his friend's pout. "Only mine is allowed to be that close to perfection."

Kennedy remained quiet for a moment as he let his anger subside. During that moment Connor mentally sized up Kennedy's appearance and had to admit that his younger friend cleaned up well when he put the effort in. Kennedy was wearing a light blue button down, gray slacks, and a navy tie. "We're like twins!"

The Boston native could only roll his eyes.

"Anything I should know before hand?"

"Dad's an architect. Mom's into design."

"Match made in retail heaven."

"Very funny K." Connor shook his head. "We better get going."

"Sure thing."

The duo exited the apartment quickly. Connor grabbed the bag Kennedy had packed for the weekend.

"Thanks again dude for well you know, everything."

"No problem bro. You've become like a little brother to me in the short time we've known each other so you might as well meet the rest of my family. You'll be calling them Mom and Dad in no time!"

Kennedy stopped walking toward the elevator as the comment sunk in.

"Come on bro, don't cry now."

"I wasn't going to," Kennedy huffed as he wiped away the beginnings of tears from his eyes when Connor wasn't looking.

Connor showed his million dollar smile once more. "Sure, just let me know if things get awkward. Dad knows a little bit, but not much. And Mom is intense to say the least."

"Thanks for being vague. That was so enlightening."

"I try," Connor said gesturing Kennedy to enter the elevator first as the doors opened. "After you."

"Don't push it."

"The button or my luck?" Connor said before the duo erupted in a fit of laughter.

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The duo took Connor's silver BMW convertible for a bit of a ride as the blonde maneuvered around the streets of New York.

"Shouldn't we be heading the other way?" Kennedy asked confused as they drove further away from the Upper East Side.

"My parents decided we're going to meet upstate tonight at the Cabin."

Kennedy could only imagine what their definition of a cabin was.

"Catch some shut eye, I imagine you'd need some after your LONG night with Chuck Bass," Connor said with a smirk as they got onto the highway.

Kennedy smacked his friend on the arm. "It wasn't like that… we kind of go back... We kind of caught up with each other last night."

"I won't pry any more. If that's what floats your boat I'll support you until something goes wrong. And I'll make sure after that we get you tested for every disease under the sun."

"That's very reassuring."

"I try Bro. Just be careful Kennedy, this isn't Boston. It's war in stilettos and blazers."

"Just what I need, even more anxiety about starting on Monday."

"Well I don't have any Xanax or weed so you'll have to make do with my mom's cookies," Connor said grabbing a tin from the back seat.

"Keep your hands on the wheel dude, kind of don't want to die now that this is beginning to get good," Kennedy said nibbling on a sugar cookie.

Connor was right, they were THAT good… So good in fact Connor nearly swerved off the road when Kennedy later smacked his hand away when the blonde attempted to relieve the teen of the tin on some windy road

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The duo arrived at "the Cabin" about three hours later. It was surprisingly modest compared to what he had expected, not that he was expecting anything simple considering who the Windsor's and what he had learned about them from an extensive use of Google.

"Take a deep breath dude, it's going to be intense."

"Meeting your parents or discussing IT?"

"Both, I'm not sure which is going to scare you more!" Connor said putting an arm around Kennedy's neck. "But don't worry I've got your back Bro!"

"Thanks Bro!"

The two did several friendly punches and other exchanges of machismo before speaking once more. They weren't at the point to me be all emotional and touchy feely.

"You may annoy me like a pesky little brother, but you're useful to me."

"You mean if I dyed my hair I would be useful for your love life."

Connor pretended to have been stabbed in the heart. The dramatics did little to help his case.

"That hurt bro."

"I try, but for some reason I feel like doing it again and again."

"Smart ass."

"I know you are."

"Seriously Kennedy?" Connor glared harshly which made the black haired male actually feel guilty and put his head down to look at the ground.

"Sorry."

"Feel better?" Connor said lifting Kennedy's head up.

"Yeah jackass, though this emotional roller coaster thing isn't as fun as I thought it would be. How it works is beyond me."

"It works all the time though."

"Still doesn't make it a good idea."

"I got you to relax. Just chill and stop talking before we say something stupid. My parents should have heard us pull up by now."

"Oh joy."

"Chill, they're not that bad dude!"

"Well they did produce you."

"And what's wrong with that?"

"Have you looked at yourself in the mirror?"

"Huh?"

"You have lipstick on your collar."

Connor began craning his neck to search for the offensive smudge.

"Someone's looking guilty right now."

"You're one to talk."

"No actually I'm not dude as there isn't any lipstick on your collar."

Connor looked angry for a moment before it subsided and was replaced by a shit eating grin.

"And the student has surpassed the teacher."

"That happened months ago dude."

"My ego!"

"We should hurry up before they think we're up to no good in your car."

"What kind of trouble could we get up to?"

"There may not have been any lipstick on your collar, but there is definitely a hickey on your neck."

"No there isn't!"

Kennedy sighed as he used his phone as a camera, taking a picture of the offensive love bite.

"Dude keep it in your pants."

Connor stuck out his tongue as he adjusted his shirt accordingly.

"You're just jealous."

"Maybe, maybe not."

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The duo was standing outside a beautiful house surrounding by various types of trees. Evergreens dotted the landscape as the leaves of maple, oak, and birch began to change color. The house was a simple looking steel blue house with crisp white trim and copper gutters. Dormers adorned the slate roof. Connor stopped right outside a beautiful iron and wood door. Kennedy was unable to put his finger on the style of the house, but it reminded him of home.

"This is it, no turning back," Connor said in a solemn tone as they stood at the door, his hand grazing his neck.

Kennedy sighed. "I guess so, I hope they like me."

"It's not like we're going out or anything dude, then you'd have to be worried," Connor chuckled.

"Thanks for the vote of confidence… and that disturbing image."

"No problem. Just be a little wary of my mom."

"What do you…"

Kennedy was cut off by the sound of the front door suddenly swinging open. He turned to see Mrs. Windsor, a very beautiful woman with a straw colored hair and a simple navy dress on. It may have been very simple but it did wonders for her.

"Connor its good to see you!" she said hugging and kissing her son.

"Mom it's only been a few weeks!" Connor said trying to act cool in front of his friend.

"You're not eating enough young man! Clearly those tins of cookies haven't been touched."

Kennedy could only smile at the antics of mother and child. He let out a mental sigh of relief. The Windsor's, or rather Mrs. Windsor was very warm and bubbly.

Suddenly he felt the spotlight being put on him.

"And you must be Kennedy."

"It's nice to meet you Mrs. Windsor."

"Feel free to call me Cassidy. There won't be any of that Mrs. stuff here. I'm far too young for any of that."

"Ok, Cassidy."

"Now that's much better," she said with a smile. "Connor's been talking nonstop about you!"

Connor blushed as the teen turned to face him… 'Maybe that dating comment wasn't as much of a joke as I thought it was.'

"Nothing bad, in fact it reminds me of when I was younger with my sisters," she said with a warm smile before embracing him in a hug. Connor could only smile as Kennedy stiffened.

"Oh sorry, I guess you weren't expecting that." Cassidy was genuinely embarrassed at how the teen flinched at the physical contact. "Why don't you two freshen up? Dinner will be in half an hour." Both boys nodded. "Kennedy, honey, you will be in with Connor for the weekend. I hope you don't mind."

And with a flourish and spin Cassidy returned to "help" her husband in the kitchen, not that Kennedy knew that, before he could even respond. While she had all the appearances of a more than capable housewife, she was far from it as he would soon learn from the Windsor men time after time.

"I don't get what she meant."

He took in the 'cabin' with great attention. While it looked quite simple it was adorned with every modern convenience in a homey way. The rich character of the original period details blended flawlessly in with the big screen tv. The outside did little justice for the interior. The past glittered in the façade, but every modern convenience was present in the lavishly designed space.

"Now you know what I meant earlier. We can talk about it later Kennedy."

"I guess… they're good… I mean, they designed this I take it? It's freakin' awesome how they did the place."

Connor blinked. "Yeah, the house has been in the family for almost two centuries. Mom took this on as her pet project after I was born. This is just the latest version and far from being the last if that's any indication... It only seems to get bigger and better with time."

"Oh."

"It's a lot bigger than I expected from outside."

"My parent's are just good like that." Kennedy laughed at the feigned arrogance. "I hope you don't mind bunking with me, but I am presuming we are having guests over if we're sharing."

Kennedy shook his head. "Your house, your rules. Just no funny business as I still remember how we woke up together last time."

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The duo walked up the spiraling stairs to the second floor. With each step Kennedy began to imagine what it would have been like to be a part of the Windsor family as photos aligned the walls.

Kennedy spaced out for a bit and continued walking, grateful Connor was carrying the bags or he would have no doubt dropped his.

"You ok?" Connor asked as Kennedy nearly tripped himself on the top step.

"Huh?"

"Dude, just chill bro. My mom already loves you… maybe more than me. It's not fair! I've been here for two decades and its love at first sight for you. I get not respect I tell you! No respect!"

Kennedy ignored the tirade at first. He had no idea of how to respond to it. Was it sarcasm? The truth? A bit of both? He wasn't sure to be honest and he didn't want to risk choosing the incorrect option.

"Very funny." The teen hesitated before asking Connor a question. He didn't want to push his luck as it was. He was intruding on the Windsor's family time after all, even if they did have something to discuss with him. They had welcomed him into their home and he wasn't about to be rude, no matter how annoying his blonde counterpart was.

"Not to sound ungrateful or anything, but how much do your parents know about me?"

Connor sighed as he opened the door to his room. A king sized bed was the star of the pale gray room. Black furniture was placed around the room in a well thought out way. Two white leather wing backed chairs were placed in front of a flagstone fireplace. That seating area was completed with a fluffy white rug.

"Why don't we take a seat first," Connor said discarding the bags by what Kennedy presumed was the closet. The blonde took the chair on the left while the guest took the other.

"Ok…"

"First of all I really have to say I hope you don't mind sharing a bed with me this weekend. I know we're chill and all but I know things are only going to get more awkward this weekend if my mom's introduction was anything to go by… And don't you think for a moment that I buy your little excuse for last time."

Kennedy blushed, but not for the reasons Connor was thinking.

"I know that you don't like a lot of touching, but it's going to kind of be inevitable this weekend. Mom is very lovey-dovey and dad is well, you'll see when you meet him."

"It won't be a big deal. At least we're not squished into a twin. Now that would be awkward," Kennedy joked.

"Yeah it would be in the morning… But back to the subject at hand, I'm not really sure to be honest. My dad obviously knows more than me as I just accepted before they finished with the proposal."

"Really?" Kennedy asked clearly impressed with Connor's initiative. He didn't even flinch at the use of the word proposal as it was obvious it wasn't the other use of the phrase.

Connor blushed. "Yeah, I've err… well I've always wanted a little brother and well you've kind of become that for me. Its kind of why I always call you Bro."

Kennedy smiled warmly as he got up and walked over to Connor, much to the surprise of the blond.

"I'm honored that you see me that way Bro!" Kennedy said as he hugged him tightly. "Not that I really like the contact, but I think you've earned it."

"You're weird Bro."

"What did you expect Connor? I learned it all from you."

"Hey! I've only known you a few weeks."

"…Well its felt like forever. Your lame jokes grow old very quickly."

Connor nodded in agreement. "I know what you mean… HEY!" Kennedy snickered. "Now my mom obviously knows a bit but I would talk to my dad later if I were you. He's an alumni and was obviously was contacted by St. Jude's. The whole thing is kind of weird how it was set up but it worked out for the two of us right? I'm sure there's an official story for you to tell your friends, but that's all I know."

"Yeah I know what you mean. So if there's a guest how are we going to do this?"

"I'll play it by ear. I think much better on my feet as you know. I'm sure my dad will seek you out if it comes to it… They didn't ask me to invite you outright, but they were both very excited when you agreed." Connor failed to mention his numerous conversations with each of his parents over the planning of this meeting.

"And here I thought you just loved my company," Kennedy smirked.

"I do or I wouldn't have invited you here now would I?" Conner countered as he looked toward the bed.

"Maybe you're just in love with me?" Kennedy said wagging his eyebrows.

"You wish" Connor said throwing a pillow.

This exchange led to an all out pillow fight as if they two were children. The duo's fight ended in a very compromising position as they heard a knock followed immediately by the door opening and the arrival of a built brunette man in a blue striped shirt and navy pants. The look was completed by a argyle tie and brown leather belt and shoes.

"You move fast Son," Mr. Windsor said. "I'll let you two finish up. Dinner's ready… I guess you'll be calling me Dad in no time Kennedy!"

"It's not what you think!" the two young adults said at the same time with respective blushes as they adjusted their clothing and hair.

"I could tell by the sound of all of the furniture falling. Be careful Kennedy, I'm sure my wife is already planning a wedding in her head," he said moving closer to the two.

Connor's jaw dropped at the thought. Kennedy could see where Connor's humor came from.

"You can't be serious Mr. Windsor."

"What did my wife tell you?"

"You never gave me you first name so it can't really apply," Kennedy retorted as Mr. Windsor smiled.

"I'm Kyle, young man," he said extending a hand while helping Kennedy up. "While Connor catches up with Cassidy later we can talk Kennedy. I'm sure there are a few questions I might be able to answer for you."

"Thanks Kyle," Kennedy replied. He was surprised at how easily things were falling into place. If he were having any doubts about the authenticity of the Windsor's before, they were beginning to stab him even harder.

"Now I'll distract Cassidy as you two clean yourselves up. Don't want to put any more ideas in her head. You haven't had a girlfriend in a while Connor so your mother is beginning to wonder… It's none of my business but I thought I would give you a heads up," Kyle said to his son who was still on the floor. Kyle turned to leave the room as Kennedy helped Connor up.

Before the door close completely, the adult peeked his head in the room.

"What you two do on your own time is between you, but remember Son, he's jailbait."

The serious look on the elder Windsor's face had the two of them completely unnerved. Yet another bout of awkward silence developed between the pair.

"Why do your parents…"

Connor glared at him. "I don't know… I guess we've become closer than we thought fairly quickly."

"Yeah… you're not…" Kennedy began blushing.

"No!" Connor said as the two headed for the door. "I just have been really picky and don't want to let them down. It's a hard feat to live down considering how storybook romantic their relationship is."

"Well it wouldn't bother me either way… especially with that big bed of your's," Kennedy said seriously looking back and forth between his friend and the bed.

*Smack*

"Don't joke like that Bro or you may have to keep an eye open at night," Connor said with a wink.

"We should really stop before this gets out of hand."

"Yeah… if my mom over hears she may think we're serious."

The two chuckled at the thought.

"I wonder who the guest is."

"It might not be anyone. THEY may think we'd be more comfortable together since its CHILLY."

"Sure dude, keep thinking that."

"Well you don't know my mother like I do. She's not very subtle."

"I'll take your word for it."

"No seriously Bro you have no clue what you're getting in to."

"I think I have enough to go on, after all you're your mother's son."

"Hey!"

"I think your dad likes me, maybe even more than you."

"That's not fair!"

"Stop acting like a five year old and get ready. I take it your mom is a stickler for the rules?"

"Kind of… They take turns playing good cop, bad cop," Conner said as he unbuckled and unzipped, tucking his shirt back into his pants and then reversing the process.

"Oh joy," Kennedy said from the bathroom, adjusting his hair and tie.

"Just don't insult the cooking."

"I wouldn't dream of it."

"No I'm serious."

"Dude…"

"Kennedy just don't do it. If you don't like something, don't make it obvious. Trust me."

"I take it you didn't eat your vegetables growing up?"

"I did… well some of them. I'm talking more about things like duck liver and quail."

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Spotted Mystery Boy in the company of Connor Windsor once again. Is there romance in their future? Or is it just another Upper East Side bromance? Mystery Boy sure is a social climber. You sure are full of surprises. Golden Boy is nothing compared to the standard of a well-bred Windsor man. You've done very well in landing such a talented companion.

XOXO, Gossip Girl

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If I get five reviews for this chapter I'll release two more chapters this week.

-Griff


	5. Holy Ground Part 2

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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Spotted. Connor Windsor and Mystery Boy going Upstate in what appears to be Connor's BMW. Now there's a handsome face that hasn't graced this site in a while. Looks like the duo are packed for a weekend getaway. Going to meet the parents already? Or will it be a romantic rendevousz in New England?

I kid Mystery Boy. You obviously have higher aspirations than THAT... Not even a month in the City and you're already doing things Lonely Boy could only dream of. Bravo. I'll be expecting an invite to the wedding. You're obviously planning something big to bring in the big guns. Who knew C and N had such interesting friends?

XOXO, Gossip Girl

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Kennedy found the whole affair was surprisingly enjoyable. Mr. and Mrs. Windsor, or Kyle and Cassidy as they preferred, were as warm and caring their son. Kyle was one of a select group notified of Kennedy's existence and jumped on the chance immediately. Good things happened to bad people. And bad things happen to good people. Kyle had not known the Blakes, but he knew that Connor had a lot to offer their son and vice versa. In the short time the boys had been together he had noticed a change for the better in his son.

It was something that made the Windsor's incredibly proud. Their son on the spot agreed to help out the orphan before they could even finish telling him what it entailed. To be honest the couple was happy that Connor could finally be someone's big brother. Cassidy had a difficult time becoming pregnant and Connor's delivery was much more complicated than expected. Sure they could have adopted, but Cassidy couldn't even imagine doing so and instead buried herself further into her work.

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The duo joined the Windsor's for dinner only to notice there were two additional (and unoccupied) place settings.

"We were supposed to be joined by the individual who did the "audit," but he had to cancel last minute. So it will just be the four of us," Cassidy said as Kyle came out with a bottle of champagne. He cut the top off with a sword that Connor would later explain was a family heirloom.

After a toast to Kennedy and his friendship with Connor the quartet began to eat their meal. Kyle apparently was a great chef, something your wouldn't expect from his demeanor. They went from soup to seafood, steak, and salad, to strawberry shortcake and several other decadent desserts he couldn't name. All and all it was really good and Kennedy was glad that he took up Connor's offer after all. This beat anything he could make or buy any day. The Windsor's made great company.

"You sure you don't want more Kennedy, you look like you could use another serving or two."

Connor chuckled at his mother mothering his friend.

"Don't you start young man! Connor, you are much to thin as well!"

Kyle could only smile at the scene before him. He had long imagined what it would be like if they were able to give Connor a sibling and it didn't seem half bad having another in their household. There was an air about Kennedy that made you immediately want to like him. He fit immediately in place… almost like a missing puzzle piece.

"Connor, why don't you help your mother clear the table while I talk to Kennedy in the den," Kyle said while giving Connor a look.

"Sure thing dad." Connor was never one to question his father. He knew THAT look and complied without a second thought.

"Do you want any coffee first dear?" Mrs. Windsor knew something was up immediately.

"No thank you Cassidy. I think it's time for MY talk with Kennedy."

The other occupants of the room made faces that did not go unnoticed by Kyle. He knew they were all dreading it for different reasons, but it had to be done. With Robert McAllister not being there, it only became more and more difficult to get this done.

"Follow me," Kyle said gesturing to Kennedy who did so.

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The two walked toward the back of the house and then down a flight of stairs before they found themselves in a wood paneled room. It didn't feel like a basement because it technically wasn't. This part of the house was a ground level addition.

"Would you like another drink?" Kyle said pouring some bourbon from a crystal decanter into a glass.

Kennedy paused to decide. He wasn't used to responsible adults offering him alcohol, but apparently this was the norm here.

"Don't worry about it. We know you won't be driving any time soon or going anywhere tonight. A little liquid courage will make this a lot easier for both of us."

"Make it a double,"

"Sure thing Son,"

The use of the word didn't go unnoticed by Kennedy. He didn't know if it was intentional or not, but he wouldn't be surprised if it weren't. After all Connor used the word Bro like it was going out of style.

"So where do I begin?" Kyle said to himself aloud.

"The beginning," Kennedy said sarcastically as Kyle smiled.

"I can see Connor's humor is rubbing off on you."

"I guess. He gets it from you after all."

Kyle chuckled as he sat down.

"Well to answer your question, it was right after the previous school year had ended. One Mr. Robert McAllister was going through the roster of new students for the following year and found your name on it."

Kennedy gave him an inquisitive look as the name didn't ring a bell.

"He's... Well he's part of administration at St. Jude's for the lack of a better term... Upon further investigation it appears that a trust fund was left for your education in care of the school. The odd thing is that there was enough left behind for four years but oddly your name was only found now and that the money was only left by a Mr. and Mrs. Blake. No first names were listed, nor was a date listed for when the funds were entrusted to the school to reserve your spot."

Kyle paused to let Kennedy comment.

"But wouldn't that have been obvious? The whole thing screams setup. No first names and money mysteriously popping out of thin air should be distinct red flags for alarm."

"I see you've caught on." Kyle smiled at the teen. Obviously the teen was just as bright as his file had read, and then some. The older brunette took a small sip of his alcohol before continuing with the tale as the teen's patience was already worn thin.

"Now Robert has been an old friend of mine for more than a little while. We may not go back to childhood, but he remains one of my closest confidants." The teen nodded in understanding as this was obviously building up to something much bigger. "

St. Jude's has a lot of scholarship students but it is not unheard of for parents to set aside money for tuition and expenses ahead of time to secure a spot in case their children's academics go south before its time for their progeny to attend. Some of your peers come to mind don't they Kennedy?"

The teen could only nod in agreement. It was quite obvious several of his peers, namely the close friends of Nate in particular, had no right in the school other than their family names and the dollars that furnished new wings of the campus and such. Money can't buy you intelligence or class, but it can help paint the illusion of some.

"What was odd was not really the lack of your "parents'" first names, but rather how the money appeared out of the blue and onto the books now. Robert went back a few years and couldn't find a paper trail of its existence."

"So there's an ulterior motive here and it's not likely Robert McAllister behind it?" Kennedy asked. "This really isn't a trust fund or an education fund is it? It was just a way to get me into the city and the school for someone else's benefit."

"I don't know. It's possible, but the odd thing was that the money literally came out of thin air. Now after Robert came across it, he contacted me and we did our research... I'm sure you hit many of the same roadblocks we have."

"My parents," Kennedy said putting the pieces together.

"I know this just became a whole lot more awkward with me being a complete stranger, but I do have your best interests in mind whether you believe me or not."

Kennedy gestured for him to continue. The adult was not sure whether he was being trusted or not at the moment, but he did not have much time to thing about his predicament as every second wasted led to another bit of doubt for the teen.

"We couldn't find a record of your parents on your birth certificate. All of your medical files were missing. Even the original copy recording your birth was missing. The copy we found was obviously doctored as your parents' names as well as those of the doctor and attending medical professionals are all blacked out."

"So there is something else going on." The teen slumped in the seat and sipped the amber liquor that burned his throat. He didn't really feel it at this point as he was too frustrated to really care about anything to be honest.

"Exactly Kennedy." The older male refilled their glasses as he paused for a few moments to collect his thoughts. "Now in order to level the playing field, Robert and myself came up with an idea... Well there's more to it..."

"The minders."

"Correct, and in fact you may now see how Connor was selected, but the others were pretty straight forward as well. Oliver Winchester and Lucas Lancaster were both scholarship students at St. Jude's that were both well liked and in need of additional aid for their college education as neither got a full ride based on their athletics or academics respectively. The two also attend Columbia with Connor making scheduling easier as well."

"That makes sense since they've always made it seem like a job unlike Connor."

Kyle smiled. "That was never our intention, but I'm proud that my son has made it less of a duty and more part of his routine."

"That still doesn't explain Mason, Kyle."

There was a bit of awkward silence. "Mason is Robert's step son."

Kyle gave Kennedy some time to process everything as he poured them another round.

"Is there something between Mason and Connor?"

"Why do you ask?"

"Of all the combinations I've seen, those two are the most awkward around each other. Lot's of tension in the air between them."

"Mason's always pretty uptight as you've likely noticed, but he's a good kid."

"I know. I take it each was selected so there would be at least one or two of them around when I'm in college?"

Kyle nodded in the affirmative.

"So what are you and Robert planning?"

"Some quiet investigating of course. No one at the St. Jude's other than Robert, the headmaster, and the accountant are aware of your fund."

"So what do they know?"

"Other than Robert and myself, no one knows that someone unknown left money in your name. The others know that the money left by your parents was misplaced along with your acceptance letter because we were unaware you were still alive. Robert and myself believe that someone is planning something bigger and you will unfortunately be a pawn in the game..."

"Does Cassidy or Connor know of this?" Kennedy asked quietly.

Kyle paused as if he was holding himself back. "Cassidy knows that I have suspicions about the delay in your acceptance, but nothing other than that. Connor only knows that you're an orphan that needed a peer to check in with him from time to time."

"Should we tell them?"

"It's your call, but I think we should wait until we have a little more info."

"I agree though I feel bad lying to Connor."

Kyle chuckled.

"You have my son so whipped. You two act more like brothers than friends. I'm glad you've been able to find some happiness."

"Thanks. Your family has been really awesome."

"It's our pleasure. You may not know this, but you've had a good influence on my son. Connor was always a bit of an air head."

Kennedy snorted.

"He was fully dedicated to his sports but little other than that, though he always managed to get good grades. How he did that I'll never know that."

"Let me guess he's all studious now?"

"Not really, but there's definitely a different air about him. He's actually taking his studies seriously."

"So what's with all the couple jokes?"

"Just trying to keep you on your toes. This isn't Boston Kennedy. You're going to have to watch what you do and who you're seen with."

"Gossip Girl? You know about it?"

"To an extent yes. It's amazing how a simple gossip site keeps better track of our children than their own parents… Its more effective and much cheaper than hiring a private investigater. But don't mention any of this to Connor. I enjoy keeping him on his toes."

"I think that's something we can agree on…" Kennedy noticed that Kyle's posture had changed as had his demeanor. "And is there something else?"

"My wife thinks Connor's gay. That's why she moved the two of you into the same room."

Then it dawned on Kennedy.

"So that's why he warned me."

"I know Connor's hasn't found the right girl yet, but Cassidy is sure that he's looking at the wrong sex completely."

"So I'm supposed to be a guinea pig?"

"No, I didn't think of that to be honest though I think Cassidy is just fond of the idea of having a gay son to shop with, not that I wouldnt put it past her." The two men shared a fit of manly laughter. "We only have three bedrooms here and the McAllister's were supposed to come so that's why I agreed for you to share a room. I didn't know there was no bed set up for you there... It's quite possible she wants to see if you two... well you know..."

"It's ok, Connor's crashed with me once or twice."

"Have you?" Kyle said raising an eyebrow causing Kennedy to sweat. "You're too easy!" Kyle ruffled Kennedy's hair. "We also figured it would be easier for you to get to know us here in the country instead of in the City. The Cabin is far less intimidating than our home in the City. Sure things seem fancy here, but they kind of pale in comparison to our normal home."

The older male smiled at the funny face the teen made while picturing the even fancier place the Windsor's called home.

"And most importantly, we chose to discuss things here as there are ears in the wall there. We may be fairly self-sufficient compared to the peers but time is money."

The teen was confused at first before he looked underneath the underneath and caught onto what the gentleman before him was implying "The help? You're afraid they've either spying on you literally or figuratively… or possibly both?"

"Exactly. Though I doubt they've gotten that far… but there are always people watching your movement when you live in a building such as ours. Sure we don't really have much use for maids, but we do other types of amenities that require employees access to our home."

"Connor's told me the same thing… Who knew you couldn't trust someone you employ?"

"Great minds think alike… The saying the walls have ears stays current for a reason," Kyle said smiling. "Why don't you head up? It's getting late."

"Don't you mean if we wait any longer Connor will come snooping?"

"Not just him, my wife is just as bad."

"What have you dragged me into?"

"You have no idea," Kyle said playing with something in his pocket. The bulge protruding from said pocket was giving Kennedy a bad feeling. But he tried to distract his mind from it as to not to give the older male the wrong impression about him. "If you ever run into trouble, you can always turn to me Kennedy. Until the day you turn 18 I will be your guardian legally speaking."

"How so?" Kennedy asked confused. This was happening all so fast.

"It was part of the deal of moving you out of state. Someone independent of, but still affiliated with the school was needed to look after you in multiple capacities."

"So you're paying for my apartment and other needs?"

"No… they're part of the mystery too. If I were paying, you would be living with Connor so he could keep a closer eye on you. The credit cards and keys in your possession and lease to the apartment arrived on my desk at work the day after Robert informed me of his discovery. It was a weird coincidence as the two of us were not on campus to be overheard by anyone possibly undercover."

Kennedy began to feel dirty by just having the credit cards in his wallet.

"So are you mad that I became your guardian without consulting you first?"

"No, its fine. It's actually pretty awesome, though I think Connor's going to be more excited about this than I am."

"Yeah… if we tell him this I'm sure he'd want me to adopt you next, not that isn't a possibility down the road."

"Wow…" Kennedy said throwing back his drink.

"Tell Connor what you want, but keep that last bit to yourself. Robert trusted myself, and Connor by extension, to keep an eye on you. I'll do everything in my power to keep you safe. It is also why I made Connor your primary minder. Though minder isn't the right word either." Kyle continued to ramble on until the teen cut him off.

"So is there anything else I should know Kyle?"

"Just focus on your studies and use this," Kyle said pulling out a wallet from his front pocket. Kennedy let out a mental sigh of relief that this was the bulge in Kyle's pocket, though it didn't make him feel much better that there were more strings attached to this deal.

"I know you have likely not used much if any at all of the stuff provided for you already, but I think it would be safer if you kept the use of that to the minimum."

"I can't possibly…" Kennedy said pushing the wallet away. Kyle pushed it back.

"I hope this doesn't come out wrong, but this isn't much to us Kennedy. Connor already sees you as a little brother and I'm sure Cassidy and myself will someday see you as a son if you let us."

The teen slumped his shoulders in defeat. There was no winning for the devil you know is always better than the devil you dont. "Fine."

Kennedy opened the wallet to find cash, a debit card, a black American Express card, keys, and a condom? Kennedy picked up the last item while pointing a glare at Kyle, to which he received laughter. How the adult knew he'd need a Magnum was beyond him, and quite frankly kind of frightened him.

"Better to be safe than sorry. You never know what kind of trouble you could get up to with Connor by your side."

Kennedy slapped his forehead in embarrassment. This was beginning to get really awkward. It was really feeling like Connor's parents were really trying to push them together not so subtly. Kennedy knew that he needed to end this before he said something he'd forget. Luckily Kyle decided to pull them another round of drinks.

"Those keys are to our penthouse and here," Kyle said. "Depending on your grades another key may be joining them in the future."

"You've got to be kidding me!" Kennedy almost squeeled at that comment. "Not that those keys aren't awesome…"

"You're going to be stuck with the Windsor's for a while Kennedy, might as well act like one of us."

Kennedy gave Kyle an odd look.

"You don't have to change beyond what you want. I just want to help make the transition easier on you as you're in a new city at a new school. Now more than ever, your clothes, looks, and decisions will be scrutinized to the most minute detail. Connor's already shown me the posts Gossip Girl's posted about you. All eyes will be on you Monday, lie if you have to."

"I hate lying."

"Unfortunately, its part of life Kennedy. If you have to, just say you're family friend of the Windsor's, which is kind of true now right?" Kyle smirked.

"Bending the truth I can do," Kennedy said wrapping his fingers around the wallet. "I am a friend of your family after all. A "special friend" of Connor's right," he said winking. Kyle nearly spat out his liquor.

Kyle's demeanor changed in a blink. There was a storm brewing behind those eyes. "Kennedy…"

"Fine… My parents were acquaintances of yours and left me in your care in case anything happened to them. Their will was only recently found, which explains why I'm here now instead of two years ago like my "education fund" would suggest."

"Now that wasn't too hard now was is?"

"No… because its kind of true."

"If you have to be seen in public, be alone with Connor if you can. Any of the others with him will rise suspicion as Oliver and Lucas in particular are far older than you and are not acquaintances of Connor or Mason. And speaking of Mason, he doesn't really stray from his circle of friends, so just stick to Connor."

"Ok."

"Now we better get back before the blondes are wondering where we went."

"Blondes versus Brunettes now are we?" Kennedy asked feigning innocence.

"I like the way you think," Kyle said finishing another glass of the amber liquid.

"Who says blondes have more fun?"

"Not us!" Kyle put a hand on Kennedy's shoulder as they headed toward the stairs.

For once he didn't mind the contact. And it wasn't on account of the Windsor's generosity either. They family just seemed so genuine and inviting. Normally he would have been turned off by the whole idea, but they were just so intoxicating to Kennedy for the lack therefore of a better word. He didn't feel like an outsider, but at the very back of his mind was the suspicion of ulterior motives.

"So can we count on you to join us more often?" Kyle said offhandedly as they continued their trek.

"If it doesn't conflict with something else… Connor and someone I met the other day are both trying to get me to play both soccer and lacrosse. I'm not really sure if I want to play either to be honest."

"And what's wrong with that? It would be a great way to meet friends and acquaintances. You won't be able to rely on Connor at St. Jude's," Kyle said stopping. "Do you want to go back to the den?"

"No, its just silly really…"

"I won't laugh."

"Well, sometimes I feel like this is all just one big dream. Everything has fallen into place so smoothly and quickly… Not to mention there's your entire family. So many things that I never thought were possible are beginning to happen."

"Kennedy, I won't pretend to say I know what you've been through, but your life hasn't been easy. You deserve some good things to happen every once in a while. Karma works for that very reason."

"I guess… I'm just afraid Connor's going to get mad once I have my own group of friends and everything… I know he's been blowing off his to spend more time with me."

"Connor's a smart boy Kennedy. He knows you will have to walk on your own two feet sooner or later. Once school picks up you'll have less free time and fewer chances to hang out together. Just do what your heart tells you. Sometimes our hearts are smarter than our brains."

Kennedy remained quiet for several moments. "That was very deep."

"Being well versed in the English language can get you everywhere Kennedy. It will get you into their hearts…"

"And their pants?" Kennedy smiled.

"That too! Just remember that life isn't all about fancy cars and designer clothes. Keep your friends close and enemies even closer. Gossip Girl is gunning for you."

"I'll do my best… we better get back upstairs before they burn down the house."

"You know, Connor inherits his inability to boil water from his mother right?"

"I'm not surprised."

"Keep an eye on your phone at all times. I know you have your secrets, and Gossip Girl has informants everywhere."

"Will do, and let me guess. If all else fails you'll get me a new one."

"Of course," Kyle smiled. "We'll need to get you the most expensive and gaudy one out there to keep up with your peers!"

Kennedy chuckled. Kyle, like Connor, was very goofy, but also very caring. He could see where THAT sense of humor came from.

"Performance over aesthetics, isn't that your philosophy in architecture?"

"You're a quick study Kennedy. Ever consider it for a career?"

Our black haired teen smiled. "Maybe once or twice. I've seen some of your work online… I'm good with my hands and have always been fascinated by it."

"Connor's never been interested, so this really is more of a deal for me than you!" Kyle said ruffling the ebony locks. "Maybe I can arrange you an internship or two as I'll have to pass off my empire to someone."

"Already sinking your claws in honey?" a female voice said from the top of the stairs.

"Maybe? Someone has to inherit my business."

"I'm not surprised, but I thought you would have at least waited for me."

"Now where's the fun in that? He's obviously not a designer. Kennedy has the brains and brawn for architecture."

An unspoken conversation was going on between the couple…

"I'll just go join Connor… I don't want to get in the way of your moment, you two silly lovebirds," Kennedy said in his most serious tone. "Teenagers," could be heard by the couple, as he continued his ascent.

The Windsor's oddly felt chastised. In that moment they felt like the children and that Kennedy was the parent who had caught them making out at the front door.

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As he headed up the stairs, Kennedy looked around the walls differently now. Where he saw design before, he now saw love. But even that couldn't not shift his attention from what had just transpired downstairs. Kennedy could still recall one part of the conversation as he headed up to Connor's room. It wasn't so shocking as it was meaningful. There wasn't much new information but he was able to gain a small semblance of closure to a degree.

Kennedy heard their distant voices as he departed for Connor's room. The blonde was likely going crazy without him. To his surprise Connor was lying on the bed shirtless and doing homework.

"What took you so long K?"

"Your dad C." Kennedy closed the door and plopped on the bed next to his friend. "Half naked for me already big boy?" Kennedy said in a husky tone.

"I thought you would enjoy seeing what a real man looks like," Connor said looking longingly into his eyes as he flexed his arms and pecs, putting on quite the gun show for the teen.

The two let out a round of laughter as they broke the silence. Their weird sense of humor just worked between them.

"So what did he have to say?"

"Not much really… there's a lot even he doesn't know, but he did say that your family has the cover of being my 'host family.'"

"Score! I get a little brother to teach all my mad moves to!"

"You're obviously getting the better end of the deal bro. I'm stuck with a complete dork."

"A dork that you love. Just admit it K."

"You're delusional C."

"We'll see about this," Connor said while beginning to tickle his friend.

Sometimes Kennedy truly felt his friend had the maturity level of a young child.

"Give up!"

"Never!" he called out as Connor continued his assault.

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Meanwhile the Windsor's were talking in the den. The two were standing by the crackling fire. It had all of the elements of a classic romantic movie moment.

"So how did he take it Kyle?" Cassidy asked her husband as she turned tp face her husband.

"Better than we expected. He's ready for more surprises."

"And did you tell him?"

"Yes… and he was quite surprised."

"I'm sure it will make sense. After all, our cover of host family will only make more sense as time goes on. 'In loco parentis' sure is handy.'"

"I guess… I just hope Connor doesn't become too attached. They're already joined at the hip Kyle. If…" Kyle cut her off with a finger to her crimson lips.

"Everything will work out honey. They're both smart kids and just what each other needed. I just hope Gossip Girl doesn't isn't up to her normal tricks."

"I still don't know why you follow that nasty chint."

"There's only so much slander… A lot of it is true and quite informative. I've already learned about how the boys are influencing each other in the past month from her posts."

"If you say so."

"I appreciate your vote of confidence Mrs. Windsor," Kyle smirked. "But I would appreciate your vote of appreciation when I rip you out of that dress."

"Oh Mr. Windsor," she said moving her hand to a certain sensitive region.

"Mrs. Windsor, you naughty girl!"

The two parents continued their little game well into the night while the two young men were blissfully unaware upstairs. Sure their family was a little crazy, but none of the Windsor's would trade it for anything.

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And there you have it folks. The end of our first two parter. Sorry this took a little longer to come out than the other chapters, but I really struggled with it. I'm trying hard not to make Kennedy too much of a Gary Stu/ Mary Sue, but part of that is necessary to the story line.

The story should start picking up a tad faster now that some more of the groundwork has been laid down for you. There's still a lot more to come. Thanks again for reading and please leave me some feedback in the form of a review. I can only improve with your feedback!

-griff


	6. White Horse

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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N spotted looking longingly out into the distance while out with C. Why so glum N? You have it all so there should be no time for brooding. It doesn't look good on you. Summer's almost over, enjoy your freedom while it lasts. Whatever that is making you sad sure isn't worth the wrinkles.

Missing B that much Golden Boy or are you thinking of Connor's buddy? You can't have everything N.

XOXO, Gossip Girl

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Nathaniel Fitzwilliam Archibald was stressed, very stressed. Nate had been spotted with Chuck and Kennedy, or Mystery Boy to Gossip Girl, and he could feel the repercussions. Blair had been extra clingy lately so he had been pushing away only for her to push back. Hearing a bit about Kennedy made him realize he had taken a lot of things for granted up until the point, his relationship with Blair being the main one.

His girlfriend would never admit it, but Blair followed Gossip Girl religiously. She loved nothing more than seeing one of her frenemies taken down a peg or too. A great shot of herself doing something that could make others jealous was another good thing in her books. She however did not like Nate being posted at all.

"I need to do some damage control," Nate muttered while playing with a credit card with his fingers.

If he had not been friends with Chuck or had met Kennedy in person, he would have believed what Gossip Girl had written. Things looked kind of couple-y in the pictures that had been submitted of them. And then there were all of the sighting of Kennedy with Connor Windsor. Now he had not been particularly close to Connor despite them being on the same soccer and lacrosse teams for two years. He knew Windsor was a good guy, but not much other than that. How someone like Kennedy could be friends with Windsor and Chuck was definitely beyond him.

Something about Kennedy intrigued him and he couldn't figure out why. Maybe it was the air of mystery, or could have it been their similar athletic preferences? He had close friends other than Chuck, but they were more of the substance using variety. He felt most at home on the field, but had no one close enough that he could trust willing to play with him…

'Maybe, just maybe I have found the one,' Nate thought adjusting his bangs. 'If Chuck is like THAT with him he has to be pretty important.'

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Blair Waldorf was angry. Wait. That was a complete understatement. She was furious. Gossip Girl had insinuated that her boyfriend was gay! Nate of all people was not gay. A little too much of a blonde, but definitely not gay. She didn't know who Mystery Boy was, but he best stay away from her circle of friends if he knew what she had in store for him.

She adjusted her signature headband as she waited to hear from Nate. He was supposed to be picking her up for their date soon. Chuck seemed a little strange in those photos. Why the two were hanging out with a Plebian, albeit an attractive one—not that she would admit that tidbit to anyone, was beyond her. Money can't buy you class, but it can help feign your social status.

"Dorota!" she yelled.

In came running an older woman in a maid's uniform. "Yes Miss Blair?"

"Has Nate called yet?"

"No Miss Blair."

"Well, let me know when he does," she snapped.

"The Windsor's are a good family Miss Blair. I'm sure this is a big misunderstanding."

"Well no one asked you."

"Mr. Nate is a very kind man. Maybe he invited HIM because he was Mr. Charles' friend?" Dorota said closing the door to Blair's room.

Blair was stunned. Her maid caught onto something she had yet to consider. It was not surprising truthfully as Dorota was more of a mother than her flesh and blood, as well as sharp as a whip. Nothing got past her maid. Maybe she was indeed looking too far into things indeed. Chuck was known to have questionable taste across the board. Dorota's suggestion did sound something like Nate would do.

A ring of her phone ended her monologue.

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Chuck Bass was used to being snarky and detached from the world. His messed up homelife and social circle had done quite the number on his health, both physical and mental. And just when he thought it would make him snap, there was the proverbial light at the end of the tunnel. Someone he had almost completely forgotten about had shown up out of the blue. And while he would never admit it to anyone, it was divine intervention. He was a more of a "make things happen" than "let things happen" kind of guy, but he was beginning to see why religion had such an effect on some people.

In true Chuck Bass fashion he was planning ways to woo his newest person of interest, in the case it being Kennedy Blake aka Mystery Boy. The Boston native was currently in the company of several well-bred Columbia men (and former St. Jude's students) that knew his dark side very well. It would take careful planning to gain their trust. And no one else would need to be focused upon than Connor Windsor, the heir of the Windsor fortune.

To be honest he could see why Windsor had become attached to the hip to Kennedy. They definitely had similar interests and personalities. Not to mention they both had a bit of a saving other people complex from what he recalled from his interactions with Kennedy and from what he had heard about the Windsor's. And ironically, right now Chuck needed a lot of saving…

"Lunch was a quiet affair but it was a good foundation," Chuck said to himself as he looked at an empty chair. "Nathaniel will serve as the perfect motivation." The Bass heir had to smile to himself. If anything they would both be thanking him later.

"Kennedy needs a friend and Nathaniel needs competition. He is far too nice for his own good and Kennedy tries to hard to please others. Oh yes things will be getting very interesting… As long as Waldorf stays away."

Chuck was not a bad guy to be honest. It was more of misunderstanding him that led to people's negative opinions of him. Once you got to know him, he was actually a pretty decent friend, well at least when you weren't on his bad side. That is why THEY kept him around.

"The only thing worse would be if Serena showed up out of the blue and got together with Humphrey," Chuck made a disgusted face. "On second thought, those two belong together. They should hole themselves together on the other side of the world in some third world location."

A ringing noise notified him of a message. Yet another blast from Gossip Girl herself. Like a lot of the more recent notifications, the source wasn't mentioned. Something was far too suspicious about it, but it didn't really reach the radar of any of our favorite Upper East Siders and Brooklynites.

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Mystery Boy and Windsor have dropped off the radar, but our lives don't revolve around them. Bromances are truly confusing things. Maybe I was wrong all along, but then again wishful thinking is always a dangerous thing… Anonymous tips are usually helpful if there is actual evidence provided. My bad gentlemen…

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"Good going Windsor, took you long enough to shake her off." Chuck ignored the second half of the blast as he went back to focusing on how to help his friend. Sure he had the money, but something was telling him that none of that would work. Kennedy neither wanted nor needed the charity. No he needed a friend right now, and that was what Chuck was going to give him.

Chuck pulled out something from a drawer. He smiled while he looked at the object. It was a simple white washed wooden box. It was so simple and plain that no one would expect him to own it, but it was dear to his twisted heart.

"Now how to set you up Kennedy. This my be my most genius plan yet…"

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…Looks like N has been buying something special for you B. Have fun tonight you two! His heart is only for you. Bromances are nothing to be jealous of. They're just nice eye candy for us ladies.

Xoxo, Gossip Girl

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Blair smiled, not that she really cared about the first half of the blast. After all there were many bromances on the Upper East Side. The one between Nate and Chuck in particular had been questioned by Gossip Girl several times already… Chuck's fashion choices did not leave much to the imagination despite the long list of women with loose legs he had managed to add to his list every week. How he managed to stay disease free was beyond the brunette queen of Constance.

Nate told her that Mystery Boy was a good guy, and if Chuck and Nate liked him he couldn't be evil right? After all, their social circle could barely exist with herself and Chuck plotting and scheming, adding another schemer with a sharp tongue wouldn't work at all. She hadn't paid attention long enough to hear Nate speak his name, but she wasn't going to ignore his presence.

"Maybe Mystery Boy isn't that bad after all." Her logic led from the picture of what appeared to be an expensive present from Nate judging from the store he was seen walking out of.

"I wonder if I should extend him an invite? He's definitely an upgrade over the Plebians like that kid who Nelly has a crush on," Blair said to no one in particular. The disgust was evident in how she thought of a certain teen from Brooklyn her academic rival had her sights set on. "He could…"

"Miss Blair!"

"Not now Dorota!"

""Miss Blair! Mr. Nate for you!"

Blair dropped her cell phone. The image of Kennedy, Nate, and Chuck fading to black as her attention shifted. The queen of Constance picked up the landline and waited for the inevitable to commence.

"Hello Nate."

"How are you Blair?"

"Fine, where are you?"

"Look outside."

Blair hesitated. This was either going to be a bad joke or something romantic. Nonetheless she stepped off her bed and looked out the window. To her surprise there stood a carriage with white horses, complete with Nate in a tux with a sign. The sign is what caught her attention. It said, "Forgive me?" in black and white.

With a flip of her hair Blair left the window (and Nate's line of sight).

'What to do?' the brunette thought to herself.

Quickly she decided on a solution. She grabbed some lip stick from last season and headed back to the window before writing a…

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Over in Brooklyn, Dan Humphrey was dreading Monday. That day marked the beginning of another school year filled of rumors and name-calling. Gossip girl had bored him lately. There was nothing there that really peaked his interesting. Why would he be interested in some new kid that was seen with Chuck and Nate? In fact the reason he felt it was boring was that his crush, the Upper East Side's own Lindsey Lohan, Serena Van Der Woodsen, was missing. She had left for boarding school and no one had heard from her for the last year. Serena was everything that an Upper East Sider shouldn't be, and that's what really piqued his interest.

"Why does that Windsor kid seem so familiar?" Dan asked himself.

"I don't know, but he sure is hot," said a female voice behind him.

"Jenny!" he shouted in surprise. "Don't do that!"

"I thought you didn't follow Gossip Girl regularly."

"Well I don't."

"Sure… That new kid sure is in a lot of sightings," Jenny said pointing to a few older posts as Dan continued to scroll down the page.

"Don't you find it odd that we still don't know his name? This is just sloppy!" Dan said stepping back.

"I know what you mean! They can figure out who's wearing a knock off, where they got it, and for how long they've had it, but they can't even come up with a name?" Jenny said going all fashion-mode on him.

"Something tells me that he's going to cause a lot of trouble Jenny."

"That's a given with Gossip Girl's obsession."

"I just wonder who he's going to cause trouble for. Hopefully its for Blair Waldorf."

"Why her?"

"Sometimes even queens need to be dethroned. There won't be a revolution anytime soon after all with the way things are right now."

Dan closed his laptop and wished his sister a goodnight as they both prepared for the first day of school. Both were dreading it, but for different reasons.

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Spotted. Connor Windsor dropping off a solemn Mystery Boy at St. Jude's. The ebony haired enigma looks like a deer in the headlights. Welcome to the Upper East Side's most dangerous locale, high school. We should have your identity by the end of the day. Stay clear of N and you should be fine. You don't want to have to deal with twice the amount of Blair Waldorf's wrath now do you?

XOXO, Gossip Girl

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Blair Waldorf was furious. That new kid in town had become the focus of many of Gossip Girl's posts, and the majority of them weren't even that mean. Heck he even got an apology… well not an outright one but she did mention that evidence was needed when submitting claims… If you read between the lines it was an apology for jumping to conclusions.

"Wow," Blair said looking at her phone. Luckily no one was around or they may have seen a bit of drool sliding down her perfectly painted lips.

The queen bee of Constance had to admit Mystery Boy cleaned up well. He was no Nate, but he looked even better in the St. Jude's uniform than her own boyfriend! She couldn't wait for the day to be over. Everyone was on edge on the first day. Not to mention she would be able to dig up dirt on Chuck's so-called friend finally. Her network of minions extended beyond the c cups of Constance and into the well filled jockstraps of St. Jude's.

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Kennedy was ready for this. He had physically been in the building a few times and met a few of his soon to be teachers. He had also met Chuck and Nate. The thing that worried him the most was lunch. It was hard enough coordinating where to seat with your friends, but doing it in a new school when the cliques are already formed is much more difficult.

He was snapped out of his thoughts by the sound of his phone vibrating. He took out to see it was a text message from an unlisted number. None of his standard tricks worked. He sighed as he was unable to trace the text back to its sender.

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Be careful. New Headmistress.

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'Oh great, now I have to deal with even more drama,' he thought to himself as he exited the text and dialed a number. After a few rings the person on the other line picked up.

"Hey Kyle, its Kennedy." The teen did his best not to sound whiny or nervous. He had something to say and was trying his best to not be immediately dismissed solely based on what it sounded like from the getgo.

"Cold feet?" The teen could picture the older male laughing at his expense.

"No just got a text from an unlisted number saying there's a new headmistress… I know something's going on, but this seems awfully convenient. Do you know anything about it? Something seems off and my instincts are rarely wrong."

There was a bit of silence before the clicking of keys could be heard in the background.

"Apparently its true. I'll be there as soon as possible."

Kennedy felt a bit guilty for pulling Mr. Windsor from work, but new it was a necessary evil. "It's not a big deal, I just thought it was a bit suspicious."

"You're right, that's why I'm coming. Changes don't happen before the first day of a new school year. Try to stay out trouble until then."

"I will do my best, but Connor's been quite the bad influence."

"Don't be a smart ass." Kennedy grinned from ear to ear. "I can imagine that young man."

"Sorry."

"Just head to the office and get your homeroom assignment from the secretary and head for homeroom. Don't do anything Gossip Girl worthy…"

"Like that even matters."

"Don't tempt fate Kennedy. Now is there anything else? I have to clear my morning for this and I would prefer not to have to deal with any additional surprises."

"No sir!" he said with a hint of sarcasm. "That's it."

"Dad would have been better, but I'll take what I can get Kennedy. Now hurry up before they start taking pictures and pointing!"

Sure enough the flashes and clicking noises alerted him to Kyle's fears. "Okay, see you soon Dad! You sure you're not watching a live feed?"

*click*

Kennedy laughed at his own joke before he groaned in pain. The teen had not got that far before he ran into Nate as he walked closer to the front door.

"It's nice to have someone else to be Gossip Girl's focus for once," Nate said adjusting his hair. Kennedy could only guess how many times a day the pretty boy did that. For such an effortless hair style, it definitely felt to the brunette that the blonde spent every free moment adjusting it.

'If they annoy him so much why doesn't he just cut them off? Those bangs are far too long. We're not in California, Surfer Boy,' Kennedy thought before shifting his attention back to N.

"Thanks man," Kennedy said glumly. "It's such an honor to have her spying on me."

Nate definitely didn't see that coming. He chalked it up to their mutual friend.

"Cheer up, can't have Chuck thinking I did something to you. For all we know it could be on Gossip Girl and he will have my head!"

"Like that hasn't already happened Nate. I've already been the subject of at least one blast by now… And scared of Chuck? Seriously dude?"

Nate shifted a bit and remained silent.

"Fine… Mind escorting me to the office then? I need to finalize some paperwork and grab my homeroom assignment."

"Sure thing," Nate said looking around before turning his gaze back at Kennedy.

"If you'd rather wait for Blair, I completely understand."

"No, I'm a man of my word. Now let me be the first to welcome you to St. Jude's," Nate said putting his arm on Kennedy's shoulder and directing their way in.

Kennedy and Nate noticed the stares they were receiving as they made their way.

In a hushed tone Kennedy asked, "Did you know there's a new headmistress? Apparently it was very sudden… Or so the anonymous text I received said."

Nate was wary of the revelation. "Are you sure? Do you get them a lot?" the boy with awesome bangs asked referring to the anonymous texts. "I haven't heard anything."

"No, I don't really. They don't come often, but when they do they usually keep me out of trouble... Kind of like my own digital guardian angel..."

And sure enough everyone's attention shifted to their phones as Gossip Girl sent out her newest alert.

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Spotted. Mystery Boy and Golden Boy mingling on the first day of school at St. Jude's. You looked very comfortable in Connor Windsor's BMW this morning Mystery Boy or should I say Kennedy? Thanks for the name drop N… Queen B will now have a name for her target. Some friend you are N…

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Kennedy glared at an embarrassed looking Nate.

"Blushing doesn't look good on you Pretty Boy," Kennedy said glancing up from his phone.

"Well it was going to happen sooner or later. Your name wasn't going to remain a secret forever… And I'm not pretty, I'm golden!" Nate's delivery was spot on, earning a giggle from some of the Constance girls mingling by some lockers.

"Why me?" Kennedy said.

"The world hates the handsome."

"Sure it does Archibald."

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…In other news there has been a big change at St. Jude's and Constance. Out with the old and in with the new. There is a new Headmistress in town and she doesn't look nice in any sense of the word.

Be careful K, don't want to mess up on your first day. I'll be watching.

XOXO, Gossip Girl

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"Here's your stop Kennedy. Do you want me to wait for you?" Nate asked as he fidgeted with his phone in hand. The fairer haired teen was unsure whether the latest notification was from his girlfriend or Gossip Girl, but he knew better than to ignore his friend so soon.

"No, don't want to give your girlfriend any more reasons to hate me," Kennedy joked, eyes targeting in on the other teen's phone.

Nate smiled. "It's too late. See you later."

Kennedy knocked on the opened door before walking in.

"Mr. Blake I've been expecting you," said a female voice said looking up from the desk as she passed him a clipboard with several forms. "Take a seat and hand it back when you're done," the secretary said glancing at a row of chairs.

"Sure."

After several minutes of giving his John Hancock and divulging personal information, he noticed the door to the Headmistress' office opened. Out came a tall and lanky male with brown hair.

"Mr. Humphrey," the secretary said as the male in question tried to make his exit as quick as possible. "Would you mind waiting a moment?"

Dan gave a forced response in the affirmative.

"I need you to escort Mr. Blake to your homeroom."

Dan only looked at Kennedy, as the ebony haired teen finished up the final lines of the paperwork.

"Welcome to St. Jude's Mr. Blake," the secretary said as she took back the clipboard and handed him a piece of paper. "You have a meeting with the headmistress during second period. Someone will fetch you then when she is ready to see you."

Kennedy nodded as Dan formally introduced himself.

"I'm Dan Humphrey," Dan said extending his hand to Kennedy.

"Kennedy Blake, but you already knew that."

"You look really uncomfortable."

"I'm sure you've seen me on Gossip Girl."

Dan forced a response out agreeing with that statement.

"I'm Mystery Boy, and you're Lonely Boy."

"Yeah…" Dan replied awkwardly.

"I don't belong here."

"I know what you mean, though at least you look the part."

"Looks can be deceiving… I just had some good guidance."

"Lucky you."

"What's that supposed to mean?"

"You're one of them."

Kennedy stopped walking. It took Dan several moments to notice his companion wasn't keeping pace.

"You have no idea what you're talking about."

"The car this morning? The posts on Gossip Girl?"

Kennedy laughed at Dan's antics. Luckily they were in an empty corridor or this would have been very embarrassing, it was far too soon to be written off as being clinically insane.

"You can say that trouble follows me wherever I go. I'm not rich if that's what you're implying. Connor's part of my host family... They treat me like one of their own if you get what I mean... I didn't ask for any of it, but they're pretty awesome like that."

"Sorry… It's just it really gets me. There's all these kids here who have trust funds and can care less about their grades, but anyone who gets in on here on merit will get overlooked for them when it comes to college."

"Bitter much?" Kennedy asked.

Dan grinned. "A little… We good?"

"Yeah… I saw your look though… I'm not from around here obviously. The Windsor's are responsible for keeping an eye on me while I'm away from home. They're kind of like my home away from home without actually being related to me."

"Like that's such a horrible predicament to be in."

"I guess it's not… but it could change fast."

"Yeah, you'll get used to things here quickly. You're already friends with two of the people at the top."

"Bitter doesn't sound good on you."

"I know."

"Want to hang out sometime? I'm kind of lacking in normal friends."

Dan laughed. "Normal doesn't happen here."

"New city, new school, new drama," Kennedy said as they continued their way down the hall to homeroom. Another blast was waiting in the wings for the gentlemen.

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Lonely Boy walking the halls with Mystery Boy. I thought you had better taste in friends K. But then again I'll forgive you because it's your first day. Things work differently here than in Boston. Status is everything and you're only as good as the car you drive.

Dump Brooklyn and dump Bass. Though the latter will be difficult as he is Golden Boy's best friend. Quite a conundrum. You couldn't stay under the radar for long could you? Be careful K or you'll find yourself alone at lunch. Connor can't be there for you all the time.

XOXO, Gossip Girl

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More's to come :D

-griff


	7. The Other Side of the Door Part 1

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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Spotted. Connor Windsor dropping off a solemn Mystery Boy at St. Jude's. The ebony haired enigma looks like a deer in the headlights. Welcome to the Upper East Side's most dangerous locale, high school. We should have your identity by the end of the day. Stay clear of N and you should be fine. You don't want to have to deal with twice the amount of Blair Waldorf's wrath now do you?

XOXO, Gossip Girl

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Blair Waldorf was furious. That new kid in town had become the focus of many of Gossip Girl's posts, and the majority of them weren't even that mean. Heck he even got an apology from Gossip Girl herself… well not an outright one, but she did mention that evidence was needed when submitting claims—something unheard of up until this point… If you read between the lines it was an apology for jumping to conclusions.

"Wow," Blair said looking at her phone. Luckily no one was around or they may have seen a bit of drool sliding down her perfectly painted lips.

The queen bee of Constance had to admit Mystery Boy cleaned up well. He was no Nate, but he looked even better in the St. Jude's uniform than her own boyfriend! She couldn't wait for the day to be over. Everyone was on edge on the first day. Not to mention she would be able to dig up dirt on Chuck's so-called friend finally. Her network of minions extended beyond the c cups of Constance and into the well filled jockstraps of St. Jude's.

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Kennedy was ready for this. He had physically been in the building a few times and met a few of his soon to be teachers. He had also met Chuck and Nate. The thing that worried him the most was lunch. It was hard enough coordinating where to seat with your friends, but doing it in a new school when the cliques are already formed is much more difficult.

He was snapped out of his thoughts by the sound of his phone vibrating. He took out to see it was a text message from an unlisted number. None of his standard tricks worked. He sighed as he was unable to trace the text back to its sender.

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Be careful. New Headmistress.

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'Oh great, now I have to deal with even more drama,' he thought to himself as he exited the text and dialed a number. After a few rings the person on the other line picked up.

"Hey Kyle, its Kennedy." The teen did his best not to sound whiny or nervous. He had something to say and was trying his best to not be immediately dismissed solely based on what it sounded like from the getgo.

"Cold feet?" The teen could picture the older male laughing at his expense.

"No just got a text from an unlisted number saying there's a new headmistress… I know something's going on, but this seems awfully convenient. Do you know anything about it? Something seems off and my instincts are rarely wrong."

There was a bit of silence before the clicking of keys could be heard in the background.

"Apparently its true. I'll be there as soon as possible."

Kennedy felt a bit guilty for pulling Mr. Windsor from work, but new it was a necessary evil. The teen already felt like such a burden, this added hiccup was really making things worse and he didn't "It's not a big deal, I just thought it was a bit suspicious."

"You're right, that's why I'm coming. Changes don't happen before the first day of a new school year. Try to stay out trouble until then."

"I will do my best, but Connor's been quite the bad influence."

"Don't be a smart ass." Kennedy grinned from ear to ear in response at the irony in the statement. Though being flippant was not in his nature, sometimes the occasion called for it. "However I can imagine that young man."

"Sorry." The teen had the decency to blush, after all he did insult the other male's son.

"Just head to the office and get your homeroom assignment from the secretary and head for homeroom. Don't do anything Gossip Girl worthy…"

"Like that even matters." Kennedy felt awkward as it was before even having to deal with the Gossip Girl angle. He was already the new kid in town which had placed a big enough target on his back, knowing the Windsor's followed her regularly added an additional level of scrutiny he wasn't sure he was prepared for.

"Don't tempt fate Kennedy. Now is there anything else? I have to clear my morning for this and I would prefer not to have to deal with any additional surprises."

"No sir!" he said with a hint of sarcasm. "That's it."

"Dad would have been better, but I'll take what I can get Kennedy. Now hurry up before they start taking pictures and pointing!"

Sure enough the flashes and clicking noises alerted him to Kyle's fears. "Okay, see you soon Dad! You sure you're not watching a live feed?"

*click*

Kennedy laughed at his own joke before he groaned in pain. The teen had not got that far before he literally ran into Nate as he walked closer to the front door.

"It's nice to have someone else to be Gossip Girl's focus for once," Nate said adjusting his hair. Kennedy could only guess how many times a day the pretty boy did that. For such an effortless hair style, it definitely felt to the brunette that the blonder male spent every free moment adjusting it.

'If they annoy him so much why doesn't he just cut them off? Those bangs are far too long. We're not in California, Surfer Boy,' Kennedy thought before shifting his attention back to N.

"Thanks man," Kennedy said glumly. "It's such an honor to have her spying on me."

Nate definitely didn't see that coming. He chalked it up to their mutual friend for no one relished the attention of the mystery blogger, not even his girlfriend Blair who was at the pinacle of the social pyramid of Upper East Side society.

"Cheer up, can't have Chuck thinking I did something to you. For all we know it could be on Gossip Girl and he will have my head!"

"Like that hasn't already happened Nate. I've already been the subject of at least one blast by now… And you're scared of Chuck? Seriously dude?"

Nate shifted a bit and remained silent.

"Fine… Mind escorting me to the office then? I need to finalize some paperwork and grab my homeroom assignment."

"Sure thing," Nate said looking around before turning his gaze back at Kennedy.

"If you'd rather wait for Blair, I completely understand."

"No, I'm a man of my word. Now let me be the first to welcome you to St. Jude's," Nate said putting his arm on Kennedy's shoulder and directing their way in.

Kennedy and Nate noticed the stares they were receiving as they made their way.

In a hushed tone Kennedy asked, "Did you know there's a new headmistress? Apparently it was very sudden… Or so the anonymous text I received said..." He began motioning his arm to offer his phone, but Nate gently refused it. The subtle exchange was hopefully innocent enough to observers as to not pay too much attention to them.

Nate was wary of the revelation. "Are you sure? Do you get them a lot?" the boy with awesome bangs asked referring to the anonymous texts. "I haven't heard anything."

"No, I don't really. They don't come often, but when they do they usually keep me out of trouble... Kind of like my own digital guardian angel..."

And sure enough everyone's attention shifted to their phones as Gossip Girl sent out her newest alert.

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Spotted. Mystery Boy and Golden Boy mingling on the first day of school at St. Jude's. Thick as theives already? You looked very comfortable in Connor Windsor's BMW this morning Mystery Boy or should I say Kennedy? Thanks for the name drop N… Queen B will now have a name for her target. Some friend you are N…

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Kennedy glared at an embarrassed looking Nate.

"Blushing doesn't look good on you Pretty Boy," Kennedy said glancing up from his phone.

"Well it was going to happen sooner or later. Your name wasn't going to remain a secret forever… And I'm not pretty, I'm Golden!" Nate's delivery was spot on, earning a giggle from some of the Constance girls mingling by some lockers nearby as they rounded the corner to the main office.

"Why me?" Kennedy said.

"The world hates the handsome."

"Sure it does Archibald."

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…In other news there has been a big change at St. Jude's and Constance. Out with the old and in with the new. There is a new Headmistress in town and she doesn't look nice in any sense of the word.

Be careful K, don't want to mess up on your first day. I'll be watching.

XOXO, Gossip Girl

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"Here's your stop Kennedy. Do you want me to wait for you?" Nate asked as he fidgeted with his phone in hand. The fairer haired teen was unsure whether the latest notification was from his girlfriend or Gossip Girl, but he knew better than to ignore his friend so soon.

"No, don't want to give your girlfriend any more reasons to hate me," Kennedy joked, eyes targeting in on the other teen's phone.

Nate smiled. "It's too late. See you later."

Kennedy knocked on the opened door before walking in.

"Mr. Blake I've been expecting you," said a female voice said looking up from the desk as she passed him a clipboard with several forms. "Take a seat and hand it back when you're done," the secretary said glancing at a row of chairs.

"Sure."

After several minutes of giving his John Hancock and divulging personal information, he noticed the door to the Headmistress' office opened. Out came a tall and lanky male with brown hair.

"Mr. Humphrey," the secretary said as the male in question tried to make his exit as quick as possible. "Would you mind waiting a moment?"

Dan gave a forced response in the affirmative.

"I need you to escort Mr. Blake to your homeroom."

Dan only looked at Kennedy, as the ebony haired teen finished up the final lines of the paperwork.

"Welcome to St. Jude's Mr. Blake," the secretary said as she took back the clipboard and handed him a piece of paper. "You have a meeting with the headmistress during second period. Someone will fetch you then when she is ready to see you."

Kennedy nodded as Dan formally introduced himself.

"I'm Dan Humphrey," Dan said extending his hand to Kennedy.

"Kennedy Blake, but you already knew that."

"You look really uncomfortable."

"I'm sure you've seen me on Gossip Girl."

Dan forced a response out agreeing with that statement.

"I'm Mystery Boy, and you're Lonely Boy."

"Yeah…" Dan replied awkwardly.

"I don't belong here."

"I know what you mean, though at least you look the part."

"Looks can be deceiving… I just had some good guidance."

"Lucky you."

"What's that supposed to mean?"

"You're one of them."

Kennedy stopped walking. It took Dan several moments to notice his companion wasn't keeping pace.

"You have no idea what you're talking about."

"The car this morning? The posts on Gossip Girl?"

Kennedy laughed at Dan's antics. Luckily they were in an empty corridor or this would have been very embarrassing, it was far too soon to be written off as being clinically insane.

"You can say that trouble follows me wherever I go. I'm not rich if that's what you're implying. Connor's part of my host family... They treat me like one of their own if you get what I mean... I didn't ask for any of it, but they're pretty awesome like that."

"Sorry… It's just it really gets me. There's all these kids here who have trust funds and can care less about their grades, but anyone who gets in on here on merit will get overlooked for them when it comes to college."

"Bitter much?" Kennedy asked.

Dan grinned. "A little… We good?"

"Yeah… I saw your look though… I'm not from around here obviously. The Windsor's are responsible for keeping an eye on me while I'm away from home. They're kind of like my home away from home without actually being related to me."

"Like that's such a horrible predicament to be in."

"I guess it's not… but it could change fast."

"Yeah, you'll get used to things here quickly. You're already friends with two of the people at the top."

"Bitter doesn't sound good on you."

"I know."

"Want to hang out sometime? I'm kind of lacking in normal friends."

Dan laughed. "Normal doesn't happen here."

"New city, new school, new drama," Kennedy said as they continued their way down the hall to homeroom. Another blast was waiting in the wings for the gentlemen.

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Kennedy followed Dan into their homeroom and was met with many stares. The homeroom teacher didn't say much and gave him his schedule. He followed Dan and sat in a seat by the window.

"Looks like we have a few classes together." Kennedy didn't pay much attention.

"Yeah, we do."

"How did you end up in FOUR APs?"

"I'm that good?"

"Seriously Kennedy, almost no one does two let alone four... In fact Nelly Yuki had to beg to get into her five and she's an actual certified genius... You're also in Honors English with me... How are you Chuck Bass's friend?" Dan applauded himself mentally for the way he snuck in the question at the end. In fact he was pretty damn impressed how he got all of that in edge wise.

Kennedy on the other hand was kind of frightened with how well the other brunette was able to sneak in so many loaded questions without anyone else paying any mind to them... Maybe the whole not being rich thing was an angle he would need to play up if he wanted to remain under the radar for the rest of his time at St. Jude's. For some reason he got the distinct impression this Nelly girl was someone he should get acquainted with quickly if Dan's comments were any indication.

"Oh ye of little faith, I'm more than good looks..." Kennedy paused for a moment to check whether or not any one else was paying attention to their conversation. Luckily Dan's status as a non-rich nobody was worth it's weight in gold as everyone else was too glued to each other or their cell phones to actively listen in on their conversation.

Kennedy let out a mental sigh before continuing. "All I will say about Chuck is that I know him from my childhood… And I'm a genius of hardwork so don't be surprised when I kick your ass academically... I had no clue I was taking four AP's but I can juggle them and my honors no sweat... I'm a lot smarter than I look."

Dan gave him an odd look.

"Knowing Chuck or my intelligence? Which one is harder to believe Dan? I know we just met but I thought you would have a better first impression of me than that... That is unless you're already influenced by the blasts on Gossip Girl about me."

Dan looked guiltily to the teen before replying: "Chuck."

Kennedy smirked as he had done some digging of his own during the previous few days. There was no way he was going in clueless when he had Gossip Girl's arsenal of juicy tidbits to educate him on the social intricacies of St. Jude's/ Constance.

"Pre-silk scarves." That was all the teen had to say to get the Brooklyn teen to approve.

"Gotcha... though its kind of hard to imagine him without them."

"It's easier than you think.

The teens laughed for a bit at St. Jude's bad boy's expense. It continued like that for rest of homeroom. The duo kept talking despite all the stares that began to be directed their way once people put two and two together and realized that Gossip Girl's latest target was sitting amongst them in their homeroom. Kennedy could care less, but Dan looked a little uncomfortable at the newfound attnetion directed his way. Sure it wasnt particularly deserved, but there were much worse ways it could have been earned. The duo went out the door at the sound of the bell and prepared to head their separate ways as they each headed to their first class of the day.

"Chemistry is down the hall and two floors down. Second door on the left."

"Thanks. See you in AP Writing," Kennedy said before extending his arm. The teen was mentally grateful for the fates for setting him on the correct path so early on in the day. He had already seemed to have made a new friend and wasn't going to look like a complete idiot trying to get to class on time.

The duo headed their separate ways after Dan broke the handshake. Kennedy was surprised when he got his schedule. He had honestly thought he had finally escaped chemistry only to find that he had some how placed in AP Chemistry… Though there were some even worse decisions made without his input on the document before him. He had some serious talking to do with Kyle…

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Lonely Boy spotted walking the halls with Mystery Boy. I thought you had better taste in friends K. But then again I'll forgive you because it's your first day. Things work differently here than in Boston. Status is everything and you're only as good as the car you drive.

Dump Brooklyn and dump Bass. Though the latter will be difficult as he is Golden Boy's best friend. Quite a conundrum. You couldn't stay under the radar for long could you? Be careful K or you'll find yourself alone at lunch. Connor can't be there for you all the time.

XOXO, Gossip Girl

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Happy Pre-Valentine's Day my lovely followers. Will you be my Valentine? If so please don't be a stranger, I will take presents in the form of reviews :D

The timing of the plot could have been better, but I figured Nate's attempt at wooing Blair was as close to V-Day as I could get with them still not having started school yet.

This is the first entry in another multiple part chapter arc. It's longer than the previous one and will pick up a tad quicker in some ways.

-griff


	8. The Other Side of the Door Part 2

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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Chemistry…. You really do have chemistry with a certain Upper East Sider. I don't know who you're praying to for good luck, but you sure have it. You're handsome and smart, don't blow it K. You only get one shot at first impressions.

XOXO, Gossip Girl

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Kennedy was surprised to see the room already half filled when he entered the room. He had not spent much time dawdling with Dan, but these rich kids didn't appear to be the punctual type to the teen even if they were in this AP course. Several were too engrossed in their phones or other techno gadgets to seem like the type to be here. A few of the students darted their eyes back and forth between them when he entered the room. Apparently being a nerd didn't mean you didn't follow Gossip Girl regularly.

'This is growing old,' he thought as he chose a lab bench in the back. 'Take that assholes. Try staring at me now without being completely obvious!'

"This seat taken?" a familiar voice said, snapping Kennedy out of his thoughts.

"No, no one's sitting there Nate… Wait... Hey Nate," he said looking up to see the dude with great bangs. The brunette was embarrassed that he had just made a complete fool out of himself in front of his friend and the onlookers.

"Are you any good in chemistry?" Nate asked in a very serious yet casual tone. Yet again Kennedy thought that Nate was living on the wrong coast with his surfer boy hair and mentality. Nate had no place in New York, let alone this AP Chem class, but he pushed those thoughts away as he tried to come up with a good response without sounding too rude.

"I wouldn't be here if I wasn't," he said confidently. Truthfully he was really stretching the truth to be honest. He wasn't half bad in the subject, but it was far from being his ace in the hole academically.

"Thank god!" Nate said seriously. "You've just saved my life dude."

"You're welcome?" Kennedy was wicked confused to say the least. Nate hit him like a Mac truck head on.

"This is one of the only AP's I could get in... And in fact, even then I had no clue I was even in it until this morning when I got my schedule so I really need the help like you couldn't even imagine Kennedy. I'm so screwed!"

Kennedy could only mentally sweat drop at Nate's declamation. He took it in stride and decided to move onto more pressing matters. Something about the way the other teen sad screwed brought a smile to his face.

"Ahh… So are THEY always like this to the new kid?" Kennedy whispered, changing the subject and shifting his line of sight to the other students who were failing at trying to discreetly look at them... Because there is no real discrete way to continually peer at the new kid sitting at the back of the class without sitting in the same row.

"Pretty much. People don't really leave St. Jude's unless their parents go bankrupt or if they get sent to rehab," Nate said glibly as they waited for the teacher to come in. Kennedy could imagine the former, but he had a hard time imagining someone leaving to go do a stint in rehab at their age, but filed it away as one of many rich kid problems he would encounter throughout his tenure as a student. "We've all been going to school together since preschool essentially, so anytime there's a new player in town it's a mad dash to get them first."

Kennedy just gave him a look in disbelief. He was beginning to wish that he was back in Boston if he was going to be seen as a proverbial piece of meat. However part of him was glad that Nate staked his claim when he did. Their conversation was cut short when the instructor came through the door and began class right on time.

"Welcome back students. Summer is over so turn off all cell phones and prepare to take notes. You will be having a group quiz at the end of the class with your lab partner so please pay attention to whomever is seated next to you as they will be working with you for the remainder of the year."

"Thanks again," Nate said as he began doodling in his notebook.

'This is going to be a long year,' Kennedy thought as the chalk screeched across the blackboard. This was going to be a long year for the teen. Sure it was a different school, but you see one boring teacher lecture on their syllabus, you have seen them all. Nate doodling during the lecture did little to help his confidence.

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Despite the doodling, Nate had actually been helpful with some of the answers much to Kennedy's surprise! The Boston teen was actually kind of guilty that he had made the assumptions he had made. Sure Nate would suck when it came to needing notes, but the other teen apparently was good enough at picking up things that he could goof off instead of taking notes...

In fact he surprised the teen even further when Nate helped with two further questions, one of which our ebony haired friend couldn't figure out despite paying attention to their entire lecture. Kennedy didn't want to know how Nate knew the answer to THAT question so quickly, but he did have a bit of a gut feeling. And as the teacher began collecting the quizzes, he stopped at Nate and Kennedy's lab bench.

"Mr. Archibald, you better keep up. I would like to maintain my pass rate if you wouldn't mind. " Nate flushed red at the comment as several of their peers snickered. "It wasn't an easy decision to make, but don't make me regret this."

The teacher wasn't exactly subtle in his comments. Apparently it was even more legal to say biting comments to students here despite the financial arsenals the pupils came from.

The middle aged man then turned his attention to Kennedy. "And you must be Mr. Blake. I was quite surprised to be receiving another student on such short notice, but it did even the numbers to allow entrance for Mr. Archibald so I do hope the two of you keep up nicely… Though it shouldn't be too hard for you Mr. Blake." Several heads turned slightly or shifted completely to eavesdrop.

"I've heard that you studied under one of my colleagues. How is Michael?"

It took Kennedy a few moments to realized who his chemistry teacher was talking about as said instructor in question never went by their first name. The other students turned slightly to hear more of the conversation going on in the back. Nate and Kennedy could hear the clicking of cell phone buttons despite the whole no cell phone speech at the beginning of class.

The older man was half paying attention to what he was saying and half checking the quiz Kennedy had filled in with Nate. The instructor was oblivious to the blatant violation of his no cell phone rule in the lab. The lack of respect for authority was appalling but the teen couldn't fault his peers either with how rude and demeaning this educator was.

"He's doing fine, Mr. Pizer. I just found out he acknowledged me in another one of his articles that was published recently. The fifth this year if I'm not mistaken. How do the two of you know each other?"

The power struggle was even more obvious now, but the teen took the point for the time being. He had one upped his teacher enough to end the round early.

"That's good to hear… Mr. Archibald you lucked out today. Mr. Blake helped you earn a 110%, the only ones in the class in fact," the teacher said turning his attention to the other students as their cell phones quickly fled out of site. "There's hope for you after all." And as the bell rang, he fled from the classroom just as quickly as his students.

"You ok?" Kennedy asked Nate. Sure the blonde had the whole laid back surfer mentality, but a verbal dressing down like that could unnerve a soldier and Nate didn't appear to be the type to take it well.

"It's nothing," Nate said shoving things into his bag.

Kennedy glared at Golden Boy, which caused Nate to brush the bangs out of his face and eventually spill. He wasn't going to take no for an answer and Nate was going to have to get used to it quickly if he wanted to pass the course.

"Mr. Pizer just doesn't like me… Or rather my father." Nate didn't say anything else and Kennedy didn't press further as it was neither the time nor the place to go into such a conversation. He would get his answer at some point, but not right now. The brunette made sure to file away that tidbit of information away in the back of his mind.

"Oh…" Kennedy wasn't sure how to reply to that as they obviously didn't have the time to do so and Nate didn't seem interested in doing so either.

"I owe you now dude right? I kind of feel bad for doodling now."

"You still helped earn it in the end Nate. I should be thanking you too!"

"Sure," Nate sarcastically replied. He bit his lip before proposing something that would make any of his close friends faint. To be honest, if anyone captured this for Gossip Girl he would profusely deny this ever occurred.

"Study buddy?" he asked with a look Kennedy couldn't resist.

"You better pull your weight or your ass is mine."

"Don't worry I'll do whatever you tell me to do if it gets me a passing grade."

Kennedy smirked in response. He could almost swear that was meant to…

"I've got French next."

"I'm off to AP Latin."

The lacrosse captain could only stare at him in disbelief…

"You're such a nerd!"

"At least I'm not a dumb jock."

The two chuckled after some awkward silence. By then everyone else had vacated the room and the surrounding vicinity.

"I'll get you for that later, but you want to head up three floors and take the third door on the right. See you in Gym!" Nate said as the duo grabbed the last of their things and took their separate paths to their next classes.

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Kennedy didn't recognize anyone here and no one seemed to care about him either, which was fine in his opinion. He did mentally thank his friend for the directions as he barely arrived in the nick of time. For a moment he thought Dan was in this class with him, but when the individual turned his head, Kennedy was proven wrong. The teen had to suppress a blush when the doppelganger caught him staring.

The class was much smaller… almost half the size of his AP Chemistry class. He thought he had left this dead language behind in Boston, but the nightmare class of his past had followed him. And even worse than chemistry, was the fact that he actually hated the dead language. The only plus side to the class was that there was a young female teacher that was quite attractive. She was in fact very easy on the eyes, and combining that with her voice made the class almost tolerable.

Chemistry he could tolerate as he had a bit of a knack for science, but he despised Latin. How we got into AP Latin was even more beyond him… This was turning into an even bigger prank… Luckily for Kennedy, a third of the way into the class, Kyle Windsor appeared. Of course his teacher remembered his son and that wasted a good ten minutes.

"Mr. Windsor, what brings you here?" asked the young teacher. "Connor graduated a few years ago if I recall."

"Sorry to interrupt Ms. Harmon, but I'm here for Kennedy Blake."

She struggled for a moment to find him, but couldn't. Kennedy stood up and gathered his things as he took this as his cue to leave.

"Of course," she stuttered while shuffling some papers on her desk. "This is the assignment for tonight."

Kennedy took the piece of paper and followed Kyle out of the room.

"Once again, I'm sorry for the interruption Ms. Harmon but the Headmistress wishes to speak with Kennedy."

"I won't get in her way. Good luck gentlemen," the teacher said fidgeting. The other students were too focused on their work to pay much attention.

The two males walked out the door, Mr. Windsor closing it behind them.

*click*

The duo walked out in the hallway after Kennedy got the homework assignment from the blushing teacher and immediately let out sighs of relief, but for different reasons.

"Kennedy, breathe."

"Who decided to put me in AP Chemistry AND Latin? Writing and Biology I get, but those two?"

"I thought you wanted those, your transcript definitely implied that."

"What are you talking about Kyle?" Kennedy asked confused.

"Six honors classes, and your elective sheet from your former school for this school year."

"I never filled out an elective sheet at my last school! And even if I did, I would have dropped Latin in a heartbeat! What kind of sick joke is this?"

Awkward silence enveloped the two males once again before they came to the same conclusion. They both got the immediate feeling that this whole ordeal wasn't as benevolent as they originally believe it to be.

"Not again," the two both said at the same time.

"The Headmistress sent me up when you never came down. Did you forget?" Kyle primped and fussed with the teen's uniform much to his embarrassment, to which he received the reply of 'Don't piss off the Headmistress even more!'

"No one came to get me, the secretary told me someone would get me."

"There's no secretary today Kennedy."

"Then how did they know we were meeting during second period? I'm fate's bitch aren't I?"

Kyle could only smirk as he patted the teen on the shoulder. He began to wonder what he had got himself into when he agreed to let Connor be one of the minders...

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"I do not tolerate tardiness Mr. Blake," said a distinct female voice.

Kennedy found himself face to face with a blonde female with a harsh face. The room was pretty average for a school administrator. Little had changed since he was last in the room.

"Sorry for the delay Headmistress Queller, but apparently there was a mix up. Whomever was at the front desk this morning told me that someone was going to be sent for me. I assumed she was the secretary when she gave me paperwork to sign."

"What paperwork?" The Headmistress was clueless to what he was talking about but hid that fact on her face. The tone in which she posed the question was bordering on rude.

"Your predecessor told me that I had additional forms to fill out on my first day to finalize things as I was accepted too late to attend orientation. I filled out a packet that had St. Jude's seal embossed it and everything this morning… I assumed because she was at the front desk that she was the school secretary because who else would have access to such documents?"

"Young man…" Kyle had enough of this and cut off Headmistress Queller. There was no way he was going to let this pencil pusher talk to his charge this way.

"With all due respect Headmistress Queller, it seems pretty obvious that something foul is going on here. The fact that someone was masquerading as your secretary under your nose and has Kennedy's confidential information is not going to reflect well upon your time here. Not even a full day has passed during your tenure and this could be your last."

Headmistress Queller blanched. She had not considered the repercussions on her end. She did not plan on Mr. Windsor being here either. This could be her undoing and she would become the educational administration laughing stock of the city, if not state.

"As Kennedy's guardian while he attends St. Jude's, I am holding you responsible for this breach of security and mishandling of protocol." The headmistress' poker face did not give away much. "Kennedy, was there anyone else here in the office with you?"

"Yeah, Dan Humphrey was here."

"Oh, yes he was talking to me this morning," the headmistress added.

"So that narrows things," Kyle said coolly. "Anything else?"

Kennedy thought for a moment. "She looked at a list and then told me my homeroom and then gave me this," he said fishing a piece of paper from his pocket.

"One moment gentlemen," Headmistress Queller said as she summoned Dan over the intercom.

"Did you look over the paper Kennedy?" Kyle asked.

The teen blushed. "No I forgot about it completely after I started talking to Dan."

He broke the seal and unfolded the paper and paled before passing showing it to Kyle and the headmistress.

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I know your secret.

It won't be a secret for long.

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"Is this some sort of joke?" Headmistress Queller shouted, completely forgetting that such a seal was only available from a board member or herself.

Kennedy just remained silent. This was quickly spiraling into a teen drama. They weren't sure who it was directed at, but now they knew the headmistress was also hiding something.

"Are you accusing him of something Headmistress?" Kyle inferred while putting a hand on Kennedy's blazer clad shoulder. "That's a St. Jude's seal embossed on that page if I'm not mistaken. And since it was given to him, I don't understand why it unnerves you so. If anything my ward should be the worried one. Are you hiding something Headmistress?"

This tense moment was interrupted by a knock on the door. In walked a confused Dan Humphrey.

"Is there something I can help you with Headmistress Queller?" Dan asked.

"Can you recall what happened after I dismissed you this morning?"

"A woman at the secretary's desk told me to escort Kennedy to homeroom and handed him a piece of paper."

"Did you recognize her?"

"Yeah, I never got her name, but she's been at that desk before, as well as a substitute once or twice too I think? She knew who I was, so I didn't think much of it either as I've seen her there a few times as I've already said." Dan continued to go on about her appearance as he shifted in his chair. Kyle and the headmistress were both beginning to grow even more worried concerning the problem at hand.

"What we have discussed is going to remain before the four of us until I get to the bottom of this. If this turns out to be a prank you two have concocted, I will expel both of you!" she said before Kyle tore into her once more, leaving her visible shaken. Dan was completely oblivious to what had transpired before he arrived, but Kyle's verbal attack was enough to help him put together the pieces as parental figures rarely unleashed verbal smack downs of that caliber on educators.

Kennedy had never seen Kyle so angry, and he hoped he wouldn't again. It was one of the scariest scenes in his life and that was saying a lot considering he had seen a lot in his short lifetime. He just hoped Connor didn't inherit that temper...

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Kennedy sighed as he wandered the halls. Class would be over soon so there was no point of going back to Latin. Kyle had left and he knew Connor would be waiting right outside when school ended. Dan had been sent back to class right before Mr. Windsor had ripped the headmistress a new one. The teen had both new found respect and fear for the businessman.

'And I thought finding someone to sit with at lunch would be my biggest problem,' thought the teen as he headed to his next class. Unfortunately he didn't have writing with Dan for another period or he would be talking with the boy from Brooklyn right now.

Kennedy was snapped out of his thoughts when he bumped into something.

"Sorry," he said immediately helping up the other person as soon as he got back up on his own two feet.

"It's ok, I wasn't watching where I was going either. You must be new if you wandered into one of the Constance halls accidentally," the female said.

"You're very perceptive." Kennedy tried on one of those smiles Connor had shown him. "I'm Kennedy Blake, and who are you fair maiden."

The female could only giggle at the theatrics. But she had to admit to herself that it was nice to be in the spotlight for once for something other than her theatrics.

"I'm Nelly Yuki. Now you better back track six doors and then take a left before one of the teachers see you or they'll think you're the new Chuck Bass."

There was an awkward silence as the two went their separate ways. On Nelly's side, it was pure shock that the new kid had taken a liking to her on first sight. Kennedy couldn't believe he found his fellow "genius" so quickly and by accident because he couldn't navigate himself around the building.

"Yuki, wait," Kennedy said surprising himself at this new found courage... Well enough courage to stop her, but not enough to use her first name.

The Asian genius turned around with a perplexed look upon her face.

"Would you like to get a coffee or something some time?"

"Sure, but you better get going, classes should be ending any minute now," she said turning quickly to hide her blush.

Kennedy could hear the clicking of her shoes hitting the floor as he made his way back to one of the St. Jude's corridors. Eventually he made his way to his next destination. Unbeknownst to the teen, another blast was making its way around both sets of hallways. Gossip Girl had found her latest target and was sinking her claws in even further.

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Upper East Siders, can you believe how much more perfect Mystery Boy gets with each passing day? First the Windsor's, and then it was Golden Boy. But wait a minute, there is something else, looks like K has a thing for Nelly Yuki. Be careful B, the tides are shifting. You really know how to make waves K, especially with a certain blooming bromance. You will be at the top before you know it.

XOXO, Gossip Girl

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This is where things really begin to diverge from the show... Ill do my best to stick to the show where I can, but the impact of having Queller show up earlier is much bigger than leaving her where she did in the show. Hope you enjoyed this.

-griff


	9. The Other Side of the Door Part 3

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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K's a magnet for trouble. In the principal's office after not even two full classes into the school day? And Lonely Boy is involved too? Mystery Boy, you sure a magnet for trouble, as well as a great source of drama. I don't think I will be running out on any news surrounding you any time soon. This is shaping up to be the best school year on the Upper East Side yet!

And I thought the day couldn't get any better? I thought him making his move on Nelly Yuki today was going to be the talk of the town. But I guess I was wrong. Now he's some soccer standout? What more surprises can we expect in the coming days?

XOXO, Gossip Girl

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'AP Biology,' he thought to himself. 'At least they hadn't messed this up.' He would never admit it, but he did like science. It didn't come naturally, but he did enjoy learning about how things worked.

The Boston teen was quite surprised to see a familiar face waiting for him in the classroom.

"I suddenly feel that my GPA is going to improve so much this semester!"

"I haven't agreed to anything yet Archibald."

"I'd bet my bangs, but we already know you're saying yes."

Kennedy sighed, it was an easy way out after all. Nate may not be a great student from the impression he had so far, but juggling two classes with Kennedy would be too much for Nate or any other sane person to gamble on.

"People are going to suspect we're friends or something," Kennedy said pulling out a notebook.

"We're going to be great friends!"

"No doodling this time or your bangs will get it," he said making a scissor cutting motion with his fingers.

"I'll be a good boy," Nate said like a child as he brought his hands to his bangs.

"I take it AP sciences aren't very popular here based on what you said before?"

"Yeah, Government, History, you name it. Anything else but science basically… and math."

"So are you better in bio than chem?" Kennedy asked as other students began to file in. He recognized one or two faces from his Chemistry and Latin classes.

"Yeah, but not by much. I can handle the dissections if you want. That's one thing I can actually do. I can do the practical but not the theoretical… I'm a hands on learner dude."

"Disections?"

"Didn't you do them at your old school?"

Kennedy didn't know how to respond to that. "There wasn't a lot of emphasis put on science… I think I was absent the day they did them on earthworms.."

"Oh, I've got you covered though. I may not be the best at naming things but I'm good at dissecting animals."

"Do I even want to know?"

"No, but I'm telling you anyways. Two words. Hunting trips."

It dawned on Kennedy what Nate meant as the duo prepared for another boring lecture. No matter where you go there will always be boring teachers, but the students will be the same on the inside. Nate may have seemed like quite the carefree dumb jock at first glance, but the brunette was quickly learning that his first impression of young Mr. Archibald was incorrect. Sure he may not be very studious, but there was a brain deep down if you could catch his attention long enough to utilize it in a productive manner.

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The duo parted ways after another "enjoyable" class. True to his word, Nate paid attention and took notes. Luckily there was no pop quiz or he would have got an extreme sense of déjà vu.

"Can I see your schedule for a second?" Nate asked as he stopped the other teen in the hall and pulled out his own.

Kennedy unfolded his own and held his own right next to the other teen's.

"Looks like someone's been looking out for you dude as we also have Math and Gym together later."

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[u][b]Kennedy's schedule[/u][/b]

AP Chemistry

AP Latin

AP Biology

AP Language and Composition

Lunch

Precalculus

Honors English

Gym

[u][b]Nate's schedule[/u][/b]

AP Chemistry

French

AP Biology

English

Lunch

Precalculus

Government

Gym

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"Basically every other class," Kennedy said a bit surprised. Things were beginning to look up as he had a familiar face in most of his classes now.

"You have AP Writing next, so you won't see myself or Chuck there."

"I figured as much."

"Well this is going to sound weird…"

"Just spit it out Nate, I'm going to be late."

"Well stick close to Dan Humphrey, he's not a bad guy... He's a shoe in to be in that class... I don't really know him, but he's not too bad with soccer either if you ever want to play a game… He's not like Chuck or me… If you get what I mean..."

Kennedy was a little confused, but then realized Nate must have seen Gossip Girl's latest blast.

"A lot of other people give him a hard time for not being rich, but he's not that bad. I don't really know him, but he's been in a few of my classes. Everyone knows he wants to become the next Hemmingway. We're not friends, but I don't pick on him either."

"He seems pretty nice, see you later Nate."

"Thanks again, Blair's going to be so happy dude!"

For some reason Kennedy's stomach did not like that and he felt a little queasy as Nate let those words out. He couldn't put a finger on what it was, but it did not settle well with his stomach.

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Writing was next and it wasn't much of an affair. He chose a random seat and sure enough Dan was next to him not long after. The two got along pretty well, but he definitely began feeling like Switzerland. Nate and the Windsor's were Britain and Dan was Ireland. He knew relations were very brittle and didn't want to be caught in the middle.

"You okay?" Dan whispered as the teacher turned around to write something on the blackboard.

"Can we do this later?" Kennedy said annoyed. "Now's not the place."

Dan got the picture and did not press any further. The duo sat in silence for the rest of class as the teacher kept going on his expectations and rules for the course. Kennedy was beginning to wish he was back in Chem. He tried to focus, but his attention kept drifting elsewhere.

"Ready for lunch?" Dan asked as the bell rang.

"Sure," Kennedy said. He was glad that Dan was in his next class as well. It made the whole finding somewhere to sit for lunch less awkward… And speaking of his next class, he was interesting to see the Nate-Dan dynamic that he was told of.

The duo quickly retreated to their lockers before reappearing outside the 'dining hall' with their lunches.

"I'll follow your lead," Kennedy said as Dan directed them to a table, well aware there were many eyes on him.

Dan picked up on this also.

"Why me?"

"Excuse me," Kennedy responded.

"Of all the people, why did you befriend me?"

Kennedy smiled. "You're the first friend I made within these walls." He began eating some fruit as Dan let it all sink in.

"Seriously?"

"Yeah… though would you care to mention why you failed to mention we had Math together?"

"It slipped my mind… the honors and AP classes are all that really matter here. Most of the other teachers are tenured jokes."

"So true, so true," Kennedy said as the duo ate the rest of lunch in relative silence, unaware another group of eyes were watching his action attentively.

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"What does he see in Humphrey?" asked an annoyed Chuck Bass to a certain pretty boy.

"Dan's not that bad, I keep on telling you that Chuck. Even Kennedy can see it," Nate added before taking a swig of his drink. "Money doesn't tell you everything about someone."

"I'm chalking it up to Kennedy latching onto the first friend he's made here."

"Maybe you're right," Nate said. "But then again you could be jealous."

"Me, jealous of Humphrey? I'm Chuck Bass!"

Nate could only shake his head. "Admit it you're jealous. Even I have classes with him and you don't have a single one."

"You won't ever replace me Nathaniel."

"Wouldn't dream of it Charlie," Nate said snatching Chuck's last steak tip.

If glares could kill, Nate Archibald would have been dead on first glance. He was so glad he had a few more classes with Kennedy, after all Chuck couldn't have revenge if he was Kennedy right? And besides the whole Charlie thing, why hadn't any of them thought of it before? Kennedy was turning out to be a blackmail gold mine.

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Precalculus, the bane of every high school student's existence… well those who aren't mathematically gifted or aren't forced to progress to Calculus proper. Kennedy was already beginning to think of ways to butter up Nelly Yuki to tutor him. He sucked at math and Nate and Dan didn't seem to be much from the looks of it. Speaking of Nate, the dude with surfer hair had arrived in the classroom first, which was a feat within itself.

"Kennedy over here!" Nate said waving a little too enthusiastically, especially considering no one else was in the room.

"You can sit with him you know," Dan said awkwardly.

"Aren't you two supposed to be fri… acquatainces?"

"Yeah, but you know…"

"Stop being such a girl, we can all sit together…" Kennedy said as the duo walked toward Nate. "The three of us could be dubbed A Gossip Girl Boy Sandwich if SHE ever got a picture of this. Golden loneliness filled with mystery."

Nate could only chuckle at the new kids antics.

"Sounds pretty good K. Don't you think D?"

"Please tell me we're not doing this right now, I can already feel my brain cells dying."

"Stop being a spoilsport Dan," Kennedy said as he chose the middle seat of the table Nate was sitting at.

"I'm surprised to see you here Nate," Dan said innocently.

Nate blushed sheepishly. "I've turned a new leaf! I'm not going to smoke THEM during math anymore!"

"Anymore during math?" Kennedy asked menacingly. Nate could see his friend was channeling his girlfriend without ever meeting her.

"Thanks a lot Dan."

"You're welcome," Dan said not really paying attention.

"Can we just stop this before anyone else gets here." The other two nodded. "I'd swear the two of you are acting like you were fighting over me or something."

Nate and Dan laughed.

"Don't piss off your study buddy gentlemen or I'll kick both of your asses on the field as well as in the classroom."

The Upper East Sider and Brooklynite both paled.

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The rest of the class went on with much disaster. True to his word, Nate was paying attention and taking notes to the best of his short attention span. There was still some doodling, but not much more than anyone else. Meanwhile Dan was really trying to understand what angle Nate was hitting Kennedy with. While Archibald was a good guy for an Upper East Sider, he was also Chuck Bass' best friend. And that was raised a red flag in and of itself.

So while his two friends were busy half paying attention, Kennedy was struggling to keep pace with taking notes. He hated math more than almost everything else in his life. Kennedy was simply horrible with numbers… well beyond basic math. He just didn't have the patience for it.

Before they knew it the class was over.

"Wow, that wasn't too bad," Nate said stretching.

"Try not sleeping for ten minutes. I'd rather not be your pillow," Kennedy replied annoyed.

"But you're so comfy!"

"And you drool."

Dan could only face palm. "Come on, English is on the other side of the building."

"Sure thing," Kennedy said as he turned to Nate. "Behave yourself," he scolded.

"I'm a big boy," Nate said adjusting his hair.

Dan smirked. "And that nap in math class was so mature?"

"You got me, I'll get you in Gym."

"Keep dreaming Archibald."

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English was just as boring as he expecting. While an improvement over AP Language and Composition and Precalculus, it was still painful despite having Dan there to keep him awake.

"You're so editing my papers," Kennedy whispered as their instructor turned their back to write on the board.

"What do you have to offer me?" Dan replied.

"Umm… why would you need anything besides my awesome friendship?"

Dan scowled as Kennedy went back to listening to about the procedures and expectations for their honors class. Kennedy was beginning to wonder if his benefactor's ulterior motive was to torture him through education above anything else.

'I can think of something,' Dan thought to himself looking at his friend.

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"Head back toward the dining hall," Dan said pointing Kennedy in the right direction of the gym. "The smell of sweat should lead you in the right direction."

Kennedy laughed. "That's the one thing that proves we're all the same."

"Didn't think of it like that."

"We're all horny teenagers trying to fit in a world we don't fit in."

Dan smirked. "That was so deep."

"Sarcasm suits you well."

"Don't get whipped too badly, Nate's quite competitive."

"What's the worst that can happen? A few cuts and bruises?"

"Be careful what your wish for man," Dan said walking away.

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Kennedy was surprised at the sight of the locker room. He was expecting something extravagant more along the lines or country clubs or even those of professional sports teams. Instead he found a typical locker room: cinderblock and metal lockers.

He attempted to find a locker in a discrete section to get it over with, but his plan was thwarted by a "Hey Kennedy, over here!" It was kind of difficult to ignore that,

"Hey Nate," Kennedy said grabbing an empty locker to Nate's right.

"So this is HIM?" another male asked.

"Kennedy Blake, meet some of my friends."

"Anthony Avuldsen." "Charlie Dern."

Kennedy nodded as each of them introduced themselves. His first impressions were not that good. While each had that All-American look to them, Anthony keep taking swigs from a water bottle that obviously did not contain water while Charlie kept playing with something in his pocket that Kennedy hoped wasnt what he thought it was.

'They couldn't be…' he thought to himself. '…Then again this is Nate we're talking about.'

The foursome left the locker room to enter the gym itself. Being on the top floor of the building allowed it to have huge windows and lots of natural lighting.

"What do you think we're doing today," Anthony slurred as his adjusted a bit of his white blond hair.

"Lacrosse if we're lucky," Nate smiled.

"Bring on the basketball," Charlie added.

Kennedy just felt out of place, beyond the normal. While everyone he had met so far had been really nice, it was hard to repress the urge to think that everyone had an ulterior motive for doing so.

"Hey Blake, what do you think?" Anthony slurred.

'Functioning alcoholics in high school? Now I've seen everything,' Kennedy thought.

"Soccer." The trio looked at him confused. "First of all everything so far has been accomodating to me, that and the soccer balls on the ground," Kennedy pointed to the equipment strewn on the floor.

"You better be wearing cups today gentlemen, as the winner's get to choose our itinerary for the rest of the semester."

The boys blinked before letting those sink in. The coach was letting them play dirty and cheap shots to their equipment would be allowed.

"How would we know to wear cups when they're not even on the uniform let alone jockstraps," Kennedy whispered to Nate. "Didn't think of lending me one while I changed now did you?"

"They were part of the freshman list, not that anyone really wears them in soccer let alone anything besides baseball. Don't worry I'll protect your goods," Nate whispered back with a shit eating grin.

"Stop it pretty boy or I'll think you were flirting with me," Kennedy laughed.

Nate blushed.

"I was only messing dude… You better be careful, you're not wearing one either," Kennedy said pointing to Nate's shorts. The tell tale sign of a cup, the prominent bulge, was missing.

"I never do."

"Brave man. I wonder what your girlfriend would say if you lost your swimmers."

The sides were formed pretty quickly. Nate's trio grabbed him up immediately and then the two sides began figuring out positions for the players. This gym class had mainly lacrosse and hockey players so it wasn't too hard to set things up.

Seeing no one else wanting to do it, Kennedy took up the goal surprising Anthony and Charlie.

"Nothing's getting between my legs," he said that made Anthony almost spit out what was in his mouth.

"We'll see," Charlie mutter low enough only for Anthony to hear.

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"And the winners are the team lead by Archibald."

"Thanks Coach, but we couldn't do it without our goalie," Nate announced as he patted his friend on the back both literally and figuratively.

"You're right," the coach said as all eyes fell on Kennedy. "Ever think about of trying out for the team Son?"

"A bit, a certain someone's been bugging me to," he said with a glare, which went completely unnoticed by the coach.

"You should definitely consider it. You have natural talent for being a goalie."

"Thanks," he said blushing while trying to play it off and seem cool to the others. The whole being praised by a teacher and his peers simultaneously was a new thing for the teen.

"Well gents hit the showers and I'll be expecting your choices by the end of the week Archibald." The coach began putting the gear away as the students headed into the locker room.

"Great job out there, you outshined ever Nate!" Anthony said as he finished off another water bottle. "And that's a feat in itself."

"You should really try it out, it would help you with the ladies," Charlie added as the quartet got to their lockers.

"I'll think about it," Kennedy said kicking off his sneakers.

"Don't think, just do," Anthony said as he slammed his locker shut, walking away in his boxers with a towel in hand.

Some students were more eager than others to get naked and shower. Nate and Kennedy lingered with small chit chat while their friends took the plunge right away, their clothing scattered all over the place.

"Your friends are nice, though…" Kennedy cut himself off before sounding rude.

"I'm two steps ahead of you. We can talk about it another time, now's neither the time nor the place," Nate said wrapping a towel around himself and stepping out of his boxers. "You coming?"

"In a minute, guess I tied them too tight today," Kennedy replied fidgeting with a knot.

"Your loss, all the hot water will be gone soon," Nate said with a wink.

'And he wonders why people think him and Chuck are an item,' he thought as he continued to play with the knot.

As soon as Nate was gone, the knot came undone instantly. He stepped out of his clothing and wrapped his towel around himself before relieving himself of his remaining garments.

"Some things aren't meant to be seen by others," Kennedy said to no one in particular as he noticed his phone vibrating, signaling that he had a new text message.

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Bro, hurry up and hit the showers K. Dad called me this afternoon. Family meeting tonight. I'll be outside to get you in a bit. Make sure you're squeaky clean or I'll have to wash you myself.

-C

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'Is he a psychic?' Kennedy thought as he walked toward the sound of cascading water and clouds of steam.

He passed by Anthony with a dopey grin and Charlie with a sheepish look, as well as other members of both teams. Drips of water cascaded down their respective torsos as the smell of sweat still lingered in the locker room. After receiving his final congratulatory pat on the back, he made his way to the showers.

To his surprise the showers weren't as private school as expected. While they weren't communal like most high schools, they were still built for multiple people. And fortunately for Kennedy, he got one all to himself. Even though he had delayed there weren't many open showers, and the horsing around gave it away as to where people where cleaning themselves.

'Some things never change,' he thought to himself as he turned the water on and felt the warm spray of water hitting his chest.

"Kennedy," a familiar voice said interrupting his careful lathering of his body.

"Nate."

"Do you want me to wait? I never got to ask you what sport you wanted to play dude."

"Kind of busy here, can we do this later?" Kennedy replied annoyed as he turned down the water so he could hear his friend.

"Sure," Nate paused. "You have nothing to be embarrassed about by the way. It's perfectly normally to want to take a peak or prevent someone else from doing so if your ashamed of what you have... Is that why you didn't come with me earlier?"

"Can we really not do this now?"

"Fine, but expect a text later," Nate said giving up, allowing Kennedy to finish his shower and erm… finish taking care of business.

"Oh and Nate?" Kennedy called out as he turned down the spray of the water.

"Yeah dude," the faraway voice said it backtracked and came closer.

"I have nothing to hide Archibald…The same can't be said about you."

The spray hit full force against the tile as the brunette's shower continued, leaving the blonde surprised. His jaw dropped at was implied. For a moment a brief stint of fear enveloped his face as thoughts ran through his mind, a million miles a second.

As Nate got toward his locker he could see the briefest part of a shadow fleeing from THAT row of lockers. What really caught his attention was a piece of folded paper sticking out of Kennedy's locker. It was a plain piece of white paper, much like that used in schools and office buildings across the globe. The interesting thing was how it His curiosity got the better of him and he pulled it from the vents of the door.

The paper was fairly commonplace and was folded quickly as pointed out in the uneven folds. It was kind of funny that he would have never noticed it if he didn't drop his body wash bottle. It rolled across the cool floor. And when he got it in hand, Kennedy's locker was in his line of sight. The piece of paper was like a flame to a moth. There was no stopping him from taking it. Nate's curiosity got an even bigger hold of him as he risked it and read it then and there. While the note it self was fairly commonplace, it was the message that caught his attention.

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[i]I know your secret. You will need to watch your back or Archibald gets it. Not even the Windsor's will be able to help. Running away from Boston means nothing. It's time for the skeletons in your closet to come out. Don't go running or they'll tumble one by one in you're not careful. Watch your castle walls crumble once more. I'll be in touch.[/i]

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Nate grabbed the note and shoved it into his bag as he opened his locker. He took his time getting dressed as he didn't have anywhere to be any time soon. Golden Boy was snapped out of his thoughts by a tap on his shoulder.

"You okay there Nate? I thought you would have left by now," asked a concerned Kennedy as he swung a wet arm around the other teen. The black haired youth could tell something was bothering Nate.

"Nah, figured I'd wait for you. Chuck would kill me if you slipped on the floor and hit your pretty little head."

"Very funny Archibald, though to be honest I'm not the pretty one here."

"So we're using last names now Blake?"

The two of them burst out laughing.

"Admit it, you must just like seeing me half naked," Kennedy said revealing boxers under his towel.

"Damn, I was planning on whipping your naked ass with a towel too!"

"Very funny."

"I'm serious."

"Nate, quit while you're ahead. We're not in a bromance yet, so all of this borderline homoerotic stuff is getting a little creepy even for you. So I'll turn around as you get into something. It's only fair."

Said male blushed before apologizing profusely as the brunette rolled his eyes.

"I have to go meet the Windsor's for something tonight, but we can work out a study schedule or something if you, well you know," Kennedy said suggestively before moving in closer. "I like you Nate."

Nate was speechless as he could feel the other teen's breath on his face.

"You're too easy Archibald," Kennedy said moving apart and pulling a shirt over his head. "You said you think I should join the soccer team, so that's what I want in return even though I think that I can hold my own in soccer. Tutoring you in exchange for some one on one training."

"That seems fair."

"Well we should get going before people begin looking for us," Kennedy pulled Nate and dragged him out of the locker room, completely unaware of the threatening note that was residing in his companions bag.

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The boys made their separate ways, Nate to look for his girlfriend while Kennedy headed out the front door to look for Connor. Right outside in his silver car was Connor leaning on against the passenger's door, complete with signature sunglasses and styled hair. Nate on the other hand couldn't find his girlfriend anywhere. He figured that she was off plotting with her minions and decided to find someone else to hangout with when it hit the five minute mark—his attention span didn't last much longer than that after all. As the It-Guy he had plenty of people falling all over him. It was good to be Nate Archibald on campus.

"You don't know subtle do you Nathaniel?" a familiar male voice asked.

"You're just jealous."

"Are you sure? I think my skipping classes would be far worse than you skipping your's. After all I was his friend first and I have the whole martyr thing going on for me."

Nate snickered before it dawned on him. "You did this Chuck!"

"Nice to see that there are brains behind those bangs," Chuck drawled out. "Why don't we take this conversation elsewhere."

"Fine."

"Gossip Girl was sent a lot of posts about you and Kennedy today. They interested me so much that I actually went to some of my classes instead of letting those kids I pay take my place." The duo paused as they exited the building and walked outside, Chuck's car was visible from their line of sight.

"I wouldn't know, my battery died during Biology… Seriously Chuck, Chemistry and Biology? You trying to kill me?"

"You needed APs and they had openings, not to mention Kennedy needed a lab partner in both courses. It's the perfect way to get both of my friends to be well friends… You should be grateful you could get into any with your grades."

"Oh like your's are any better."

"But I'm not the one looking to go to college."

"You will be if I tell Kennedy, he sure knows how to make you bend Chuck."

Chuck scowled to which Nate smirked. "I owe a lot to him."

"What's that supposed to mean?" Nate asked confused. Chuck ignored that question and instead changed the subject. There were some things not even his best friend was privy to know about this point. He just had to make sure things went well for Kennedy or they would come to light.

"I think both of us will have to stop slacking off… Knowing him, Kennedy will make us cut back on alcohol and drugs too."

"You can't be serious."

"You've never seen him when he gets crazy while completely focused on something. It's scary and it doesn't matter whether you need to study or not, he's going to make you do it if his mind is set on it! He's eerily like Blair in that aspect. But luckily I'm not the one sharing classes with him."

"Then let's enjoy our fleeting moments of freedom. I can already feel the homework I have in my future."

"Then let's make a toast," Chuck said pouring them two glasses of an amber liquid. Nate wasn't too sure what it was as his mind was elsewhere. It was so unlike Blair not to be around after the bell. Not to mention she had yet to text him back.

"To Kennedy."

"To Kennedy, the guy that will finally boost your GPA," Chuck added, causing Nate to nearly spit out his drink. "I have no plans on making honor roll, but I'd rather suffer a few more classes than Kennedy's wrath. He's kind of scary when he gets all wound up."

"Do I want to even ask?"

"No."

"Chuck?"

"Hmmm?" he replied while finishing his swig of the liquor.

"There's something you aren't telling me," he replied knowing full well he wasn't going to get anywhere with Chuck. If you had the Bass heir's trusts, there was little that could break it. After a few seconds of hesitations, Nate took a piece of paper out of his bag. "Someone shoved this in Kennedy's gym locker as I finished my shower. I only saw their fleeing shadow as I approached. Do you know anything about this? I don't even get it."

Chuck read the note.

"How do we proceed?"

"We stay close Nathaniel."

"And keep him out of Gossip Girl's line of sight?"

"Easier said than done with all these talks of a new bromance blooming between a certain blonde and a boy from Boston," Chuck said pulling out his phone.

"Whoops."

"Oh Nathaniel don't you ever learn?" he questioned while pouring another round.

"I didn't even realize… I must have had more than I thought last night."

"Most of if is still in your system if that's any indication."

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Can mystery boy become any more perfect? From his friends to his clothes he has it all... Well except for Lonely Boy, but that's far from being a faux paus with that schedule of yours. Looks like there's brains and brawn ladies. Watch yourself Nelly or someone else will try to steal K away from you.

XOXO, Gossip Girl

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What did you think of Dan's intro? Did you enjoy the ending of this three parter? I'm hoping it was worth the wait! As a bonus for slacking off, I am posting two bonus chapters this week!

-griff


	10. Stay Stay Stay Part 1

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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Connor must really enjoy being your chauffeur K. I dare say its much cheaper too. Why pay when you can get a service that is much more personal? You certainly have a way with the handsome ones. Would you mind toning it down a bit?

Some of the ladies would enjoy having their boyfriends back… Have fun wherever you're going with the Windsor heir tonight K. I'm sure it will be fun.

XOXO, Gossip Girl

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"You don't know how to cool it do you bro?" Connor said as he turned the key in the ignition, his signature sunglasses perched on his face.

"What are you talking about?" Kennedy feigned innocence, glad he didn't have to look directly in the blonde's eyes, but at the same time nervous because the reverse couldn't be said.

"Your bromance with Nate Archibald."

"I hate that word." A chill ran down the teen's spine.

"Just be careful. Like I've said before, I don't care who you sleep with but be careful literally and figuratively," Connor lectured pulling out of his spot and driving down the street. "You and Archibald seem very cozy together by the way… I honestly can say I didn't see that coming considering everything."

It took all of Kennedy's composure not to blow right then and there, but he held his ground and let the older male continue on his lecture.

"His girlfriend is a brilliant schemer from what I've heard, definite superiority complex, but a schemer nonetheless. Oh the times… I'm so glad I'm not in high school anymore. Sure the high school drama still butts its head in my life, but its different… You actually care about what people think about you in high school. College is a whole different beast."

Kennedy was deep in thought at Connor's later statement. There was a definite nugget of truth buried deep in there, something that he would hold onto to think about at a later time. But for now he had some good news for the blonde that would not hopefully make him crash into another car on account of the glee and pride he would soon be feeling as the driver's ego inflated to the size of the Empire State Building.

"I'm apparently a natural at soccer, even the Coach agrees," Kennedy added sarcastically to change the subject. "I'm apparently a really good goalie. Nothing got between my legs."

"Well you did have my help… Not that anything belongs between your legs Bro."

Laughter was all the response Connor received. The blonde took that as his cue to continue on with his interrogation.

"How were classes?"

"I could ask you the same thing."

"Nothing big little bro, but Dad told me you have quite the plateful."

"Yeah. Four AP's and an honor's… I'm going to die between Chem and Bio alone."

"Add soccer in the fall and lacrosse in the spring and you'll either be at the top of the pyramid or a hot mess… Juggling a current seasons practices with the training for the following one will take a lot of careful planning. Thankfully Mom and Dad are good at that. I don't think I could have done it without them."

Connor didn't let the glare stop him.

"Try adding wrestling or hockey for the winter while you're at it. I'm sure you'd love to find an excuse to grind against Archibald or some of your other peers. Putting some of the bigger dumbasses on the mat is also very satisfying… And besides you'll be Gossip Girl's favorite Upper East Sider in no time!"

A hard punch to the arm ended that conversation.

"He's seemed weird around me lately. I don't know if it's because Chuck Bass told him more about my past or if he's just into making all of his friendships into bromances. Seriously dude are all athletes that err…"

The blonde male adjusted his face as he thought deeply. By he, Connor knew Kennedy was referring to Nate Archibald. It seemed like a lot of Kennedy's problems would be involving him from this point forward. Between the furrowed eyebrows and contorted chin, Kennedy didn't know whether to laugh or be scared.

"I didn't really get to know him so I can't say much… I still say he has an ulterior motive in befriending you so quickly and so easily. He's known for always getting what he wants. From what I've heard Nate isn't the best student so I'm guessing he's going to aim for you to tutor him as a friend. Though that's all contingent on his girlfriend and father. If they're complacent with where he is, then that theory goes out the window."

Connor made a sharp turn that resulted in an ever-increasing glare from his passenger.

"Sorry about that, but I'll take that as it as a yes then. And I will also take it you get one on one training sessions in soccer and/ or lacrosse with him?" Eyebrows raised and moved suggestively causing the teen to blush crimson in response. "You two sure looked cozy snoozing in precalc."

"Must you always make everything sexual. He's not even close to being my type."

"Only when it comes to you my baby brother. You're so easy to rattle." Hair was ruffled and then fixed. "Now do you feel better?"

"Yeah, but do you always have to do that?"

"Not my fault you get wound up so easily you prude. It's only the first day of school and you've already had as much craziness as Lifetime Original Movie. When should I expect a love triangle between a boy and a girl?"

A quick and well placed punch to the arm as well as a change of subject put an end to that topic quite easily as Connor spent more time nursing his sore arm instead of finding more about the basis of Gossip Girl's blasts today.

"How's your lady friend?"

"No changing the subject." Connor liked being in control. This was so not part of the plan!

"So things aren't going well?"

Connor growled before pulling his phone out of his pocket as they stopped at a red light. He threw his phone at the teen.

"Shut up and just read. Gossip Girl loves you apparently. You couldn't lay low for one day could you? Things are only going to get worse from this point on." The arrival of ringtone alerted the two males to incoming danger. "And speak of the devil, she must have some more dirt on you!"

"Eat it up you jerk. Chick's dig mystery. You're not important enough to even have an alias. You're a no one!"

Connor scoffed but turned his attention back to the road as they still had quite the drive ahead of them.

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"Do you want to do the honors?" Connor asked his "brother" as the duo came to an imposing door.

"Shouldn't you be carrying me over the threshold?"

"You two didn't tell me you eloped last night?" a female voice said as the door opened.

"Mom." "Cassidy."

"Come in now before our neighbors think you two are serious. All we need now is the Granger's spreading rumors of Connor seducing a MALE high school student to throw a wrench in things."

"Not my fault," Connor said with an innocent look. "Kennedy must have some crazy pheromone or something… He sure knows how to drive all the guys around him crazy."

"Well if YOU kept your hands to yourself…"

"Boys, we have more important things to discuss than your sordid love lives," Kyle said entering the room before adding another comment in a much lower tone. "As long as you wear condoms…"

"Sorry," both of the youths muttered as Mr. and Mrs. Windsor directed them to the living room. Kyle's second comment went over their heads but not Cassidy's. A certain sparkle appeared in the corner of her eyes.

The adults took the two club chairs while the young adults plopped down on a very comfy brown bonded leather couch. Mrs. Windsor may have been more of the type to use humor to procrastinate and avoid the inevitable, Mr. Windsor only use it to lighten the mood. Right now was one of the times he was getting straight to business.

"Kennedy, did anything seem off today beyond the obvious?" Kyle asked.

"Some of the teachers… they well looked as if they knew more about me than they should. Especially what's his face teaching AP Chemistry," the black haired teen said trying to remember that particular instructor's name. "I don't know how he knew about my old school and who I was taught by. I honestly thought he would only see my grades to see whether I was qualified or not to be taking his course. I didn't expect for him to have a thorough background check like I was some criminal or something."

"Should we scoop him out now Kyle, there are plenty of other schools… It's still early enough in the year. Riverside…" Cassidy was cut off before she could even finish her statement. Sure it was no St. Jude's but it would serve him quite well just the same if it meant he wouldn't be at the same risks, in fact it may have been even better for him considering he'd be even further at the top of the academic pyramid.

"No, I think I should let it play out for now," the teen in question replied surprising the family. "After all, that money is nonrefundable and I would rather not waste the money if I can avoid that. Whomever is behind this may react poorly if I do that, then we would have no idea of what they're up to. By staying at St. Jude's at least we can control some aspect..."

"You don't have to be brave all the time bro," Connor said embracing his friend/ brother. "It's still early enough in the school year…" Unfortunately, the blonde was cut off by a hand to his mouth. He grumbled out a few not-so-pleasantries as he was stopped before he could finish his line of thought.

"Well wouldn't staying and playing dumb be the best way to get to the bottom of it? And besides, I'm sure Chuck Bass wouldn't let anything happen to me. He's oddly protective of someone he barely knows."

"How do you know him Kennedy? He has quite the reputation," Connor asked for his parents. Sure he didn't know the Bass heir, but you didn't have to know him to know of him. Chuck Bass had quite the reputation after all. His parents may have been all gung ho about grilling the teen, but from their looks it was all up to him at the moment.

"We go back, I don't really feel comfortable going on about it right now, but you can trust him… well at least when it comes to me."

"We won't press any further on that subject then," Cassidy said glaring at her men, to which Kennedy was grateful. Though she sent a sympathetic look at her son when neither Kyle nor Kennedy was looking.

"Unless Nate Archibald gets kicked out of my AP classes, I have him or Dan Humphrey in all of my classes except for AP Latin. Both of them seem pretty trustworthy. Then again first impressions aren't everything."

"Why does that last name seem so familiar?" Kyle asked his wife. His words may have been obvious, but his eyes spoke volumes.

"I'm not sure Honey," she replied with a slight tinge of pink developing on her dimples. She had an idea where she remembered the name, but was too embarrassed to admit it.

"Archibald is a good kid for the most part Kennedy so it would be good for you to be around him. Making connections is just as important as making friends HERE. He would also be a good a way to get on both teams as he's a bit of a star on both. However we would prefer if you did not partake in his other extracurricular activity young man. He has a bit of a reputation of being a bit of a well stoner… and his grades reflect that." Kyle felt bad mouthing the teen's friend but he had to know now while the year was still fresh. An ounce of prevention is more than worth it after all.

"I understand and I'm already a few steps ahead of you!" the teen replied cheekily. "I made him promise not to use any around me if he wanted my services."

"Cheeky monkey" Connor whispered low enough so only his buddy could hear him. The tone of the teen's statement was lost on the adults, but the college student caught on quick enough. Kennedy may not have admitted it, but there was a hint of interest hidden in the not so subtle use of the word services.

"We're trading favors," Kennedy announced to the horrified faces of the adult Windsor's. The two youths had to fight the urge to burst out laughing. Suppressing their grins was quite the challenge indeed as the looks on their faces was quite frightening and hilarious at the same time.

"Not like that! What is it with this family?!" Kennedy got up from his seat and began flailing about only to be shoved back down by Connor. After a few more moments of looking like a complete fool, he regained his composure and continued. "He's helping me on the field and I'm tutoring him! I'm not that kind of guy people!"

The three Windsor's had the decency to look thoroughly embarrassed, though that wasn't enough for the teen.

"That is a good approach, as the quicker you integrate yourself, the less at risk you will be. The more allies you forge amongst your peers the better. You never now when the Headmistress or someone else in the administration or faculty could turn on you." Cassidy was still crimson at the thought of her pseudo son and his friend being together. "Making others reliant on you will help secure your spot and add lines of defense against potential threats."

"I'm not in the middle of a social war Cassidy."

"You're in high school, that should speak in enough of itself." She said it as if it were the most obvious thing in the world. Kennedy had to restrain himself from slapping himself on the forehead with how true the statement truly was.

"Touche."

"Why don't you two hit the books while I start on dinner?" Kyle asked, well more like ordered.

"Sure thing Kyle." "Fine Dad."

"I'll whip up some cookies if you two get a move on now," Cassidy said causing the two youths to trip over themselves as they darted out of the room and made a mad dash for the blonde's room. The thought of those luscious morsels of goodness was enough to make them enjoy doing homework on a Friday afternoon.

"I still don't understand how you can bake, yet any time you cook it ends in tragedy. It's just not right." Mr. Windsor whined as he watched his wife begin to make a mess of his kitchen as he worked around her to get a start on dinner.

"I don't know either, maybe it's the careful planning. After all, you can do all the work for me if all I have to do is make dessert," she replied feigning a kiss. "There is so much room for error in them that I have to be precise unlike when you cook. You have much more wiggle room based on experience."

"Honey..." A quick elbow to the small of his back was more than enough for him to stop.

"That's what you get for insulting my cooking skills."

"Keep that up and you'll be on the couch tonight!"

Mrs. Windsor had the decency to blush as he wasn't all gentleman all the time. He was not above kicking her out of the bed when she was wrong!

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"Nice room bro," Kennedy said looking from place to place.

"I'm surprised Mom hasn't redecorated yet, she sure enjoys redoing everything fairly often. And with you here I'm surprised she hasn't installed another bed in here, there's more than enough room for one."

"I'm not taking your room. I've taken enough."

"More homework, less talking gentlemen!" came from down the hall.

"How does she do that?" Kennedy asked dropping his bag.

"I don't know. Desk or bed?"

"It's your room."

"I only have reading so I can do either."

"You take the desk, can't have you falling asleep on me Connor. I know how you think buddy. It's that time of day after all you old man."

"Very funny Kennedy."

"We both know its true."

"Well… screw you!" he replied plopping down at the desk.

Connor got to work highlighting as he read over his psychology textbook. Kennedy on the other hand made himself comfy on the bed and began doing his writing homework. After a while the duo had moved onto other work.

"Hey Connor, how do you do this?" Kennedy said adjusting himself on the bed. Connor spun around on the chair and sat down next to him on the bed.

"It's not really that difficult. You're on the right track. You messed up right here though," Connor said pointing to a step in Kennedy's math. "Your final calculation is thrown off because of that."

"Not everyone is a math genius."

"Well you're oddly good in science and writing. You can't win them all."

Kennedy pouted. "Your Latin teacher still blushes at the mentioning of your name, did your dad tell you that?" Kennedy said gaining the upper hand. "What did you do or not do with her to make her so flustered and tremble as just the mention of your name?"

"Nothing at all! I'm serious Bro, but I don't know why she ever liked me so much. She's not that much older than me also so it was always weird. Sure she was wicked hot, but I wasn't going to cross that line."

"Not to feed your ego, but you're pretty hot bro."

"I know that," Connor grinned as he popped the collar of his shirt in an obnoxious way. "But it sounds so much better coming out of your mouth."

"She's so boring for such a hot teacher."

"There's only so many ways to make a dead language interesting dude… But I have to agree she's quite hot… She was the focus of many a daydream."

"Just for that you can help me with Latin too! And I think you meant wet dream!"

"What about my homework?... Wait! Why you little smart ass!"

"I thought you would do anything for your little brother."

"Fine."

"In return I'll be the one to break it to Mason there's been a change of plans. Since you obviously forgot to tell them we were coming here tonight."

"Whoops." Connor scratched his head in embarrassment. "I knew I forgot to do something today… Bro that's actually a fair trade, even if you think I even had a need for wet dreams."

"I knew you would see it that way." Kennedy completely ignored the wet dream comment.

"You're a lifesaver once again bro," Connor replied sheepishly as he went back to checking the Latin assignment..

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Hey Mason, I'm spending the evening with the Windsor's. Mr. Windsor decided on it spur of the moment. Enjoy your night off :D -K

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Not a minute later:

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No problem. Enjoy yourself tonight. Kind of forgot myself. Don't let that doofus rub off on you. -M

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"See I told you."

"I thought you called him a jerk Kennedy," Connor said not looking up from the beginnings of the translation. "You mixed an ablative absolute with an ablative of means here."

Kennedy let out a huge and silent sigh of relief as Connor ignored his phone. If Connor had seen the text, the brunette was sure the blonde would have done something really stupid. Sure Connor wasn't the brightest bulb, but his temper was kind of nasty. And unfortunately Kennedy had been on the receiving end of it not long after they first met. The teen thanked the heavens that it was only that one time. Kennedy could only picture Connor channeling that anger on the field.

"That's why I have you for." The brunette did his best to hide the ghost of a smile. The text was quite entertaining in his opinion. Kennedy knew that if he wasn't careful that Connor would be on to him and snatch away his phone.

"I still don't know how you got into AP Latin. Your translation is so shoddy and this is quite easy Bro. You're not going to survive the class at this rate."

Kennedy broke out in laughter. "This is so ironic dude. I don't know how I will either. Someone out there must really hate me to get me in... I barely passed it as it is at my old school and I didn't have a chance at going Honors., let alone AP!"

Their little heart to heart was interrupted by the matriarch of the Windsor Clan. It was just yet another moment that made them both point their finger at something that was missing out of their lives. Unfortunately neither would notice it as it was neither the first nor the last time any attempt at putting together those thoughts would be effectively extinguished like a candle in the wind.

"Boys, dinner!" a feminine voice called out ending things.

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Dinner was a fairly simple affair. Well as simple as one could get with one taking part in a meal with an Upper East Side family. Navy rimmed white fine china plates and brilliant silverware adorned a mahogany Victorian styled dining table with walnut inlay details, as the Waterford crystal glasses glistened, casting radiant reflections onto every available surface. Crisp white linens balanced the dark wood Chippendale chairs and ornate draperies. All in all, it was timeless, classic, and effortless beauty that would stand the test o of time. The imposing nature of the setting for their dinner was daunting, but the teen was ready..

"So how was school Kennedy?" Cassidy asked tossing her salad.

"It was fine," he said passing his salad plate over to her. "Definitely not as bad as a certain someone made it sound like."

"I was mentally preparing you for the worst," Connor said defensively. "It was basically as bad as I predicted right?"

"I wasn't talking about you Connor, though your description of the locker room didn't do them justice. They're way classier than anything I'm used to."

"Then who are you talking about bro?" he asked confused. In fact you could color all three of the Windsor's confused. Kennedy liked playing mind games, not that you would expect that looking at him. He kind of had the whole innocent nice guy act down to a t.

'Cue the dramatic music,' the teen thought as he prepared to start something, finally focusing his attention at the suspect in question. "Your father."

"KYLE!" "Dad!" The two blonde's went off on the older brunette just as Kennedy had planned. Kennedy was good at deflecting, something none of the Windsor's had realized just yet.

"Hey, I had the same concerns as Connor. What did I do?"

The teen smirked. 'Game, set, match.' Kennedy put it on a little thick as he quickly got to his point. "I greatly appreciated your concerns, but you laid it on a little thick."

"That's not the only thing that's a little thick," Cassidy added to lighten the mood.

"That was low Cassidy," Kyle replied as he felt the figurative stab in the back… or should we say stomach?

"So was terrorizing Kennedy. Now let's drop this before I start us all on a new dietary regimen." The Windsor men looked in horror as did Kennedy. "Now that's more like it. How do you like you schedule Kennedy?"

"Well I have an AP Latin teacher that has the hots for Connor…"

"Kennedy…"

"I'm serious Cassidy! I'm surprised she didn't seduce him when she had the chance." Connor's face was a crimson as it could get as he tried to sink even further into his chair. He didn't appreciate being brought into this once more. And even more so he didn't want to bring up those memories…

"She was tripping all over herself when she saw me Cassidy." Kyle didn't even bother looking up as he cut a tomato with his knife. "It was quite pathetic to be honest. She was like an abandoned puppy when I walked in."

"Oh lord…" Cassidy said feeling a familiar headache come on.

"Then there's AP Chemistry where the teacher has it out for my lab partner Nate Archibald who is also by AP Biology lab partner, but that class is much better. If I can get him focused on things, I'm sure we can put the stoner thing to rest, but I hope that was more of an exaggeration than actual fact... Don't even get me started on the other archetypes that are running wild through the halls of both schools... Moving on, AP English Composition and Honors English on the other hand both seem easy, but with a lot of work attached. I have my friend Dan in both of those classes so I'll have his help to fine tune things there… Precalculus, I don't know. I hate math, but I have both of them to keep me entertained."

"Well it's a good thing Connor's good at it. In fact he'll be more than happy to help you in Latin and math."

"I will?" Connor said looking up from his food.

"You will." Cassidy turned her attention to the other youth. "That is if it's ok with you Kennedy."

"I guess," Kennedy said playing with his food. He wasn't really one for salad, but he wasn't about to insult the hand that was literally feeding him. "I just feel like that either its going to be a really good year or a really bad one. From the Headmistress to some of the teachers and students, it just doesn't feel right."

Using the awkward silence that followed, the adults cleared before bring out the entree. Connor and Kennedy's mouths both watered at the sight before them. Now meat was definitely some Kennedy could sink his teeth into literally and figuratively.

"It will get better, you just have to let the New Kid Syndrome wear off a bit," Kyle lectured while cutting his fillet mignon with ease, in fact it was like cutting through butter. Kennedy smiled as he sliced through his own. 'I could definitely get use to this,' the teen thought as he listened attentively. This lifestyle was something he could certainly appreciate after so many years of struggling to get by. It was like a god send, or maybe karma?

"There's so much mystery about you, which doesn't help. And with you being admitted under the previous Headmaster that is mysteriously replaced at the beginning of the school year can only add to it. You'll be the focus of the attention of your peers, their parent's and the administration."

Kennedy didn't really know what to say. "Speaking of that, did you find out anything else about it? Headmistress Queller sure is a pain to put it nicely."

"Robert hasn't got back to me yet. And none of my contacts have found anything either. Cass, has your network dug up anything?"

"No Honey, but I do find it odd they brought in someone new instead of promoting one of the assistant headmasters at the last minute."

"All this talk of St. Jude's is making me bored. Can we change the subject?" Connor asked innocently. "I'm sure Kennedy would much rather have us talk about all of the Gossip Girl posts about him instead."

"Oh really," Cassidy said with a wicked grin that was matched by her son. "I wasn't aware you still subscribed." Connor waved it off as Kyle meanwhile sent a sympathetic look to the teen while going back to his second steak instead of getting involved with the brewing storm. "Go on Connor. I'm quite curious to see what she has to say about our little magnet for trouble."

'They're crazy, but its nice to know what it feels like to be part of a family,' Kennedy thought as he began to answer for his actions… or rather the candid portraits people captured out of context and submitted to the gossip site did so for him as Connor passed his phone to both of his parents.

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What did you think? Sorry about the lack of a posting but life has been hectic... This is the first of a bonus double post this week. I'd really appreciate feedback by the way :D

-griff


	11. Stay Stay Stay Part 2

Disclaimer: I don't own any of the Gossip Girl Universe outside of any original characters, concepts, or locations not seen in the actual books or TV show.

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C and N are plotting something… And for some reason I don't think its for B's upcoming big party… Things sure are getting interesting now that Headmistress Queller is cracking down on everything. Be careful ladies and gents, she is quite the beast. Don't put yourself on the end of her bark or you may face her bite as well. Now while I normally prefer you Upper East Siders to cause drama and scandals, you may want to tone it down for a bit or I wont have a site to run. What kind of trouble did K and N get up to for his dad to come home early? A flustered K was spotted exiting the home moments later. I need details.

XOXO, Gossip Girl

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A few days had past, and like the Windsor's had insisted, things were getting much better almost entirely across the board. Sure his AP Chemistry instructor had it out for Nate and now himself too, and maybe his AP Latin teacher was a little creepy, but for the first time in a long time he felt as if he fit in. After all who has more problems than a rich kid?

Kennedy took Connor's suggestion and told Nate that he wanted to put Wrestling on the list of sports for the remainder of the semester. It was either that or hockey, but he didn't want to be stuck in the net for another sport, though he'd probably ace that too. And besides it would be good to see if he held any promise in it before tryouts later that fall. He wasn't an overachiever for nothing! Why go for the safe bet when you could go out on a limb without being obvious?

Archibald's reaction was quite entertaining. The black haired teen had never seen his friend become so red. In the end the sports ended up being soccer, basketball, wrestling, and football in that order. All in all not too bad considering he sucked at most of them. Thankfully the boys didn't share gym with the girls or things would have been much more embarrassing… particularly for the month of November.

"Do you have time to study tonight dude? I know the test isn't for a few more weeks, but I don't really want to mess this up," Nate said kicking off his sneakers as he got his lock undone.

"I guess, we might as well work on our lab reports while we're at it too. But you're hosting."

"I always host," Nate replied stripping out of his gym clothes. Kennedy rolled his eyes. He knew full well there was little truth to that particular statement—especially since Nate crashed at his apartment more times than he count. "Just admit it, you like my food."

"Don't you mean your chef's food… and besides its more comfortable crashing at your place."

"Same difference… wait what?"

"I live in a cubbyhole compared to your parent's townhouse. If I fall asleep out of boredom it would be much better than you crashing on my couch," Kennedy added revealing his abdomen from the confines of his sweaty St. Jude's shirt. "Or your bed."

"I think your apartment is nice, though you're right about that couch. Could you have got something even harder than a rock itself?"

"YOU would think that. because there are no priceless heirlooms to be destroyed. Not everyone has money growing on trees."

"You just had to bring that up didn't you?" Nate said throwing a sweaty sock at Kennedy.

"Thanks for the appetizer Archibald, but I prefer edible food. Eau de Nate does not count as seasoning."

"Very funny," Nate replied while trying to maintain a straight faced as the duo headed for the showers, two different showers. While more comfortable around each other, neither particularly enjoyed being naked around others, let alone each other. "Most people would be fighting to get a piece of me."

Kennedy was down to business like usual. "Let's make this a quickie, we have a lot of work to do tonight."

A shadow descended upon the locker room as the boys turned on their respective showers.

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The duo arrived at the Archibald townhouse after a quick detour at Starbucks. Nate quickly learned that Kennedy was a caffeine fiend, particularly of the iced variety or rather any variety. From shots of espresso to their mixed drinks, Kennedy would drink them all.

"That was disgusting," Nate said as the arrived outside his door.

"It's not my fault I foresaw the need to amp my self on lattes and frappuccinos to get through this."

"Do you even know how many calories you just ingested?"

"Enough to be canceled out by gym and any special 'activities' you have planned for me tonight. Besides we both got some work done while there… or rather I did as you gawked at me."

"Very funny," the golden haired youth replied opening his door as he became more than a little flustered at the image that appeared in his head. "The maid and chef have the evening off so it's just us."

"You tricked me."

"Well how else would I get you to cook for me?" Nate asked with a big grin as the two settled at the Archibald dining table, one not very different from the Windsor's. "You cook way better than the help!"

"You realize that will cut into your study time right?"

"We were going to have to take a study break anyway. And besides we have plenty of time. Did you really think I was going to full on study tonight?"

"You're incorrigible."

"What does that mean?"

Kennedy sighed. He was a lot like Nate, but he could use and understand big words. "Do you want to handle Chem or Bio?"

"Chem, you're better at it but I think it would be better if we both played against our strengths."

"If you say so Nate," Kennedy said whipping out a textbook and laptop.

"What are you doing?" Nate asked.

"While normally I would suggest handwriting to get it in your memory, typing is more practical to share and edit. This way we can each get a copy of my hard work. I already started on a rough outline as we did the assigned reading, but I'll make them better now that we'll need them for the exam."

"Never thought of that, no wonder you're the genius here. I'll be right back," Nate said running up to his room.

"This is going to be a long night, maybe I should have grabbed a coffee for the road," Kennedy said out loud as he began reading the first chapter.

The sound of clicking was all that filled the room until the front door unexpectedly opened with a male coming through it.

"Nathaniel!" the voice called out, causing Nate to nearly trip down the stairs as he carried his laptop in hand.

"What are you doing here? You were supposed to meet your mother and I over half an hour ago. Your mother is very cross with you at the moment to put it lightly."

"I know I was forgetting something… Dad… I was doing homework with a friend from school."

"A very likely situation Son. Like I haven't heard that sorry excuse come out of your mouth before."

"I'm telling the truth, Kennedy here can prove it," Nate said running into the dining room and gesturing to the teen at work at the table. "See he's still here!"

Kennedy looked up from his outlining to notice a man with a striking resemblance to his friend.

"Looks like you're going to have to take a rain check Kennedy, I completely forgot I was supposed to be somewhere with my parents," Nate said completely embarrassed.

"No worries dude, Kyle and Cassidy will probably be checking in on me soon enough."

"I hate to interrupt any more, but you wouldn't happen to be talking about Kyle and Cassidy Windsor would you young man?"

"Yes, Mr. Archibald."

Mr. Archibald laughed when he heard how Kennedy addressed himself.

"Captain is fine… Sorry, I never got your name." Nate backed away a bit as he knew this was going to get awkward. His father never showed this level of interest in any of his friends right off the bat before. This was raising red flags. "I don't recall the Windsor's having any nephews."

"That's because I'm not related to them, well not that I'm aware of. I'm Kennedy Blake," the teen said getting up and extending his arm out. "I'm one of Nate's classmates turned tutor."

The Captain took the arm and shook the offered appendage. "That's a mighty strong handshake you have their young man."

"Thank you, but I should get going," Kennedy said putting away his things in his backpack. "Remember to start your outlines tonight Nate, I have two other tests next week so I wont be much help if you don't do your part too.

"Don't worry, just remember I'll meet you at the park tomorrow morning before practice."

"Nice meeting you Captain," Kennedy said as he took his cue to exit, quietly closing the door behind him.

"Nathaniel…"

"I was studying, or well trying to."

"I see that, and your performance at school has proven that so far this semester from what your teachers have told me," the Captain said as he glanced at the mess on the table.

Nate was quite surprised his father was in contact with his teachers, but then again there were no progress reports or personal notes going home this semester on account of Kennedy's influence, so his father had a right to check in. It was still early enough, but he had hidden or rather forged signatures on more than a few progress reports over the years.

Notebooks and textbooks littered the table. There were diagrams of cells and a periodic table by index cards and a study guide. The Captain quickly fingered through one of them.

"Yeah, about that…"

"I'm proud that you are finally taking things seriously Son. It's damn time you made a friend that actually cares about his studies. Maybe you'll get into Dartmouth without my help after all," the elder Archibald said with a hint of pride.

Nate didn't know how to react. He wasn't used to his father being like this. There was a genuine hint of pride in that statement.

"Maybe…"

"So how did you meet this Kennedy, I don't recall seeing him around before. And if he's connected to the Windsor's that's even more surprising. Their only child is older than you by a few years… In fact he should be in college right now."

"He's new to the city. They're playing host family to him while he attends St. Jude's. He's not from around here actually." Nate continued to babble random and useless facts that his father took in without a word.

"Very interesting," the Captain replied.

"I don't know much beyond that, but he is very serious about his studies."

"He may not have the same blood as us running through his veins Nate, but academics, determination, and the right connections can rectify that." The Captain paused as something connected in his mind. "We should get going before your mother gets even more furious."

The two Archibald men left the townhouse and made their way to Mrs. Archibald. Nate was curious as to why his father had reacted the way he had. Something was not connecting right. It was almost as if he knew something that he wasn't letting on. While he was glad to see that his father was worried about his academics, it was kind of weird how interested he was in Kennedy. After all the Captain was never that interested in any of his friends, not even the trouble causing Chuck Bass.

Nate could only hope that Kennedy wasn't too mad at him for wasting his time. While the trek between their places wasn't too horrible, it was time wasted that his friend could have better spent studying.

A text snapped him out of his self-wallowing.

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N, don't worry Connor just called and the Windsor's wanted me to come over for dinner so I guess it wasn't meant to be. Hope your dad doesn't hate me too much. He seemed really mad at you… Everything ok?

-K

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'Leave it to him to be concerned about me when he's the one that got the third degree,' Nate thought as he rode in the car in silence with his father.

A cough alerted Nate to the fact that his father wanted to speak with him, something that sent chills down his spine. His father was only good for two things: not being there and lecturing Nate about not being good enough to get into Dartmouth. The sheer fact that he had mentioned Nate cleaning up his act scared the teen. He didn't realize his father had even noticed, not that his mother was likely to either. Mrs. Archibald was a French socialite that spent her time better spent with other socialites than with her own child.

"While I applaud your new found dedication to your academics, you cannot continue blowing off commitments you do not wish to go to," the Captain lectured.

"Dad, I'm sorry, but I honestly completely forgot. I just asked Kennedy to come over because I'm really worried about AP Chem."

"I didn't know you were in AP Chemistry Nate," Mr. Archibald said interested.

"I didn't either, but apparently a spot opened last minute. Bio too."

"You are full of surprises today Nate, maybe I should have let you stay with this Kennedy. He is obviously having a good effect on you unlike Charles and the others."

Nate forced a response as he didn't feel like his father breaking down why each of his other friends didn't deserve to be associated with his son.

"There's something oddly familiar about him, where did you say he was from again?"

"I didn't, but he's from Boston."

The Captain tried to hide it, but the vaguest hint of realization dawned on his face, something his son caught on to.

"Very interesting… here's our stop Nate," he said as the car came to a stop.

Nate had a feeling this wasn't going to go well. His mother he could handle, but not the others. This was going to be a long dinner he had do say so himself.

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Spotted leaving a familiar restaurant, clans Archibald and Waldorf in their best designer duds. How are you going to break it to K, N? I thought you said you were going to put your studies first? Ditching your study buddy for Queen B? Be careful what you say, K isn't as forgiving as you Golden Boy. His air of mystery will bite you in the ass sooner or later. He's a friend of C is he not?

Be careful B, he could out scheme you. Oh wait, he already has. K is definitely proving to be a force to reckon with. Seems like C taught him well. Nelly Yuki is on K's arm, and rumor has it he doesn't like bullies or cheaters. What's this about forcing people to change their answers B? That desperate to get in Yale? So not going to happen now.

XOXO, Gossip Girl.

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The last blast had confused many of her subscribers. It alluded a lot of things but nothing at the same time. While no one thought there was anything going on romantically, the growing bromance was hard to ignore. Heck even Chuck was changing and that in itself was a scary thought to many of his peers. They didn't know whether it was genuine, a dare, or part of a scheme.

Unfortunately for everyone currently involved, Blair was not happy. Her world as she knew it was crumbling and there was one personal responsible for it, Kennedy Blake. She did not enjoy what the blast implied… She wasn't that desperate to get into Yale… she was destined to get in there with all of her connections after all.

'Someone's going to pay for that accusation!'

While she enjoyed her friend becoming more academic rather than complete addicts, she wanted to be the one in control. She was the Queen and she did not appreciate this upstart barging into her kingdom and usurping her power, quickly turning her loyal subjects against her and toward him.

He was nothing but an arrogant commoner like Dan Humphrey to her. Neither of them belonged in her world, and she wished she could do more, but it would get back to her… it always did. Her handiwork always showed, unlike that of Chuck.

"Dorota!" Blair yelled as she brushed her dark brown locks.

"Yes Ms. Blair," the Eastern European woman said running into the room.

"Where is my mother?"

"I do not know Ms. Blair. She has not returned my calls."

"Ugh!" Blair screamed, her brush narrowly missing Dorota's head. "Get out of my sight!" Dorota didn't need to me told twice.

Tonight was not going to be a good night for Blair.

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Kennedy and Connor planned on something different… it wasn't a double date, but it was a night between the "brothers" and their female companions… Well originally it was supposed to be a family dinner night, but Cassidy whisked Kyle off to some high society gala somewhere in the city. The two youths were too busy thinking of what to do instead as she listed off the details.

"I hope I look ok," Nelly Yuki said fidgeting with her dress, a gift from Kennedy, or rather the AmEx Kyle had given him.

"You look beautiful tonight. I know we've only had coffee before, but it means a lot that you'd come with me tonight," Kennedy said with a smile that made her stomach flutter. "And in that… I didn't think you'd want to wear it."

"It's not a problem."

"My life's complicated…"

"Everyone's is here on the Upper East Side. We don't do simple here."

"The Windsor's are family to me now, so I'm glad we were able to come as friends to this event."

He didn't notice the hurt look on Nelly's face, but he did realize he made a slip up. He did however make a great recovery with the grace of a cheetah ready to pounce on a zebra.

"I have a lot of fun with you, but I don't want to take things too fast. I've heard from a lot of people that many relationships often implode and are captured on Gossip Girl. I just don't want that to happen… She spends enough time on me as it is... So I'll understand if you want to end things here, but I really don't want to mess this up."

'Nice catch,' Nelly thought to herself. Her face turned pink with the delivery. He had thought out things a lot better than she had imagined. She had feared she was being strung along based on his relations with Chuck and Nate, but she was ready to get her knight in shining armor... even if he was taking the chivalry thing a tad to far.

"I'm glad too, it lets us take time to get to know each other better. If this doesn't work out I'd much better prefer the possibility of being friends than leaving not speaking to each other at the end of the day. It's a lot harder to have an intelligent conversation here than you'd imagine with all of our resources and connections at hand."

"So what do you think of contemporary art to be honest?" Kennedy asked as the duo approached a glass door, which he opened for her.

"It depends. I prefer it in sculptures more than painting. I don't really like cubism"

"I agree," he added while allowing the door to close behind him. "My 'brother' Connor's girlfriend is a bit of an artist." He made quotation marks with the word brother.

Nelly knew a bit about it from Gossip Girl and a bit from Kennedy himself, but she didn't press further. His association with the Windsor family was still up in the air, but she knew patience would pay off in the end. She would get to the bottom of the mystery when he was ready, whether they were involved with each other or not.

"I think that's a bit of an understatement," she challenged as the two teens walked into the gallery to realize the whole exhibit was for Candace.

"Kennedy!" a blonde blur cried out, nearly knocking over them both.

"Connor," he replied sternly as he regained his balance.

"And who is this lovely lady you have with you bro?" Connor asked genuinely which only caused Nelly to blush.

"This is Nelly Yuki, she's from school."

"I don't know why someone as intelligent and beautiful as yourself would waste their time with my little brother, but you must see something in him. "

Nelly was so used to being berated for being a typical Asian, so she had no clue how to respond to Kennedy and now Connor's compliments.

"Now, while Mom and Dad will be glad to see you have someone as talented as a certain Intel winner on your arm tonight, make sure you mingle. Tonight means a lot to Candace," Connor said with a certain air about him before he left to talk to someone else.

"No pressure eh?" Kennedy said seriously to Nelly.

"No pressure," she mimicked while picking up a glass from a waiter.

"I don't think I'm ever going to get used to being a socialite."

"You won't, but I don't think I will either."

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The night ended without much affair. The two teens took a taxi back to Nelly's home. He opened the door and took her hand as she exited the cab.

"I'll be right out," Kennedy told the cabbie.

"Your money," the driver replied nonchalantly as he started the timer up again.

"I don't think you'll ever know how important tonight was to me, but thanks for a great night," Kennedy said as they stood on her front step.

"I had fun tonight," she said with an awkward shift of her body."

"Me too," he added while fidgeting with his fingers.

"You can just kiss me now if you want. You don't have to ask."

"Sometimes I'm too much of a gentleman for my own good."

"Just hurry up and kiss me before my parents wake up."

In the moment that followed, both teens could feel a spark. For the first time in a long time they finally felt like they fit in with their peers.

"That was amazing," Nelly panted. "You must have made several girls very happy over the years."

"Actually, I don't kiss and tell."

"Smart ass," she said playfully smacking his arm.

"I'll see you tomorrow. Sorry that I had to take you from your studies on a school night."

"Just don't make it a habit," Nelly warned putting her key in the door.

"Is that a challenge?"

"You can be the judge of it." Nelly turned the knob and opened the door. "Good night Kennedy."

The door shut and both teens felt more complete. They both knew it would end up on Gossip Girl, but they had not done anything scandalous.

Kennedy walked down the steps and reentered the cab.

"Thanks again for waiting," he said as he closed the door.

"It's your money. Where to next?"

"Home," Kennedy said with a smile as the cab drove off into the distance.

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Gossip Girl here. Looks like Queen B's bookworm has snagged herself a prince. Buying a designer dress that hasn't hit shelves yet, kissing your hand, opening doors, and a kiss good night? It sure seems like new blood can make a world of difference. Who knew all it would take to get Nelly Yuki away from her books was a nice guy from Boston? If you could even tell me how K got that dress off the runway, it would leave me forever in your debt Nelly.

XOXO, Gossip Girl

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Dan could only look on with jealousy as another of his friends had snagged a girlfriend. Kennedy seemed like a normal kid, but now he was going off flaunting his money like the rest of them. Not that Dan could really blame him. With a girl like Yuki, you needed to pull out the stops to keep yourself off of Blair's hit list.

To make the matter even worse, rumor had it that Nelly Yuki had a crush on him! To be honest he couldn't blame Kennedy, but deep down somewhere it did feel like betrayal on some level. It was just a rumor that Nelly had a crush on him, but still it was a rumor about him, Dan Humphrey, the kid from Brooklyn. He just stood there glued to his computer screen before his phone vibrated, signaling a text message.

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Going to play a pick up game with Nate and a few of his friends tomorrow. Want to join us after school? -K

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Sure. Prepare to get your ass kicked. -D

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Haha! That's exactly how Nate responded. See ya in class tomorrow D. -K

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Dan put his phone down and closed his laptop. While he was jealous to an extent, he was more than happy for his friend, at least one of them was getting a shot at happiness... And if he played his cards right maybe he'd get one of his own. Kennedy was far too perfect to be true, but he proved everyone wrong time and time again. He did the impossible and Dan wasn't going to be left behind. He was ready to take advantage of the waves.

'Maybe there will be someone for me,' he thought to himself as he headed to bed.

He would eventually regret that wish for a storm would soon unfold the social landscape of the city with one simple text.

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Blair Waldorf was prepared for WWIII. One of her minions had defied her again. But then again maybe this was exactly what she needed.

"I may have the perfect scenario now… Nelly you're safe for now. In fact you may be even rewarded. You will be the perfect pawn."

*Knock*

"Ms. Blair do you need anything else?"

Blair gave a sound of disgust. "You are dismissed for the night Dorota."

"Yes, Ms. Blair."

When the footsteps were far enough a sinister smile crept upon the headband queen's face.

"I'll be able to do so many things under the guise of being a friend now… They won't know what hit them."

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Chuck Bass was never one to really care about Gossip Girl, but the latest blast had left him intrigued.

"I did not think you had it in you," Chuck said to no one in particular.

"Who are you talking to?" a female voice said as she shifted up right in the bed, the sheets barely covering her nude form.

"No one," he said with a grin.

"Then care to make this a round four?"

"I thought you would never ask," he replied with a devilish smile as the pair battled beneath the sheets once more for dominance. Lips clashed and legs interlocked. Chuck Bass had better things or rather women to do than his homework.

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Meanwhile a certain dirty blonde looked at things with a not so happy outlook. Things were not going the way they wanted and they knew just how to make things exactly how they wanted. It was only a matter of time.

A few clicks of a keyboard and it was now done.

Upon closer inspection, one could see what had just transpired:

The blonde sent something to Gossip Girl. And from the looks of it, it wasn't going to be pretty. The Upper East Side wasn't going to know what hit them.

Out with the old and in with the new… The return of an old friend? Or was it the arrival of a new enemy?

It all depends on who's involved.

In a few days time the Upper East Side was going to wake up to something big… something that would make Kennedy's arrival and ascent to the top look like child's play. No this was going to be Emmy worth.

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Prepare for trouble and make it double. You're going to need protection from the upcoming devastation for it won't unite all the people within Gossip Girl Nation. Be ready to denounce the evils of truth and love, which extend their reach beyond the stars above.

JessieJames98 just sent me a doozy. Be patient.

When the time is right, a bombshell will be unleashed you will never recover from.

XOXO, Gossip Girl

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Like the Pokemon reference? And thus concludes the bonus postings for a total of three new chapters this week.

-griff


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